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Chemical Structure| 850222-40-1 Chemical Structure| 850222-40-1

Structure of 850222-40-1

Chemical Structure| 850222-40-1

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Product Details of [ 850222-40-1 ]

CAS No. :850222-40-1
Formula : C13H19NO2
M.W : 221.30
SMILES Code : O=C(C1=CC=CC(OC)=C1)[C@@H](C)CN(C)C
MDL No. :MFCD09753761
InChI Key :YHCVGGJYRMYIGG-JTQLQIEISA-N
Pubchem ID :25146676

Safety of [ 850222-40-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 850222-40-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 850222-40-1 ]

[ 850222-40-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 850222-41-2 ]
  • [ 850222-40-1 ]
YieldReaction ConditionsOperation in experiment
96.5% With diethylamine In tert-butyl methyl ether at 20 - 25℃; for 1.5 h; 2. Preparation of (S)-3-(dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1- one (Ia); <n="21"/>(S)-3-(Dimethylamino)-1 -(3-methoxyphenyl)-2-methylpropan-1 -one (2R,3R)-O,O'- dibenzoyltartrate (968 g, 1.67 mmol, ee 98 percent) was suspended in tert-butylmethyl ether (6 L) in a 10 L double jacket vessel equipped with an electrical impeller stirrer, a gas transition line, R100 temperature measuring equipment and an oil based cooling/heating system and diethylamine (384 g, 5.25 mol) was added. The reaction mixture was stirred at 20 0C to 25 0C for 90 minutes and a solid was siphoned off. The filtrate was concentrated at a temperature of 40 0C in vacuo until a pressure of 4 mbar was reached. (S)-3-(dimethylamino)-1-(3-methoxyphenyl)-2-methylpropan-1- one was obtained as a colorless oil (356.7 g, 96.5 percent, ee 98 percent).
References: [1] Patent: WO2008/12047, 2008, A1, . Location in patent: Page/Page column 19-20.
[2] Patent: WO2008/12283, 2008, A1, . Location in patent: Page/Page column 8.
[3] Patent: WO2008/12283, 2008, A1, . Location in patent: Page/Page column 9.
[4] Patent: US2011/190267, 2011, A1, . Location in patent: Page/Page column 67.
  • 2
  • [ 50-00-0 ]
  • [ 37951-49-8 ]
  • [ 506-59-2 ]
  • [ 850222-40-1 ]
YieldReaction ConditionsOperation in experiment
78% With hydrogenchloride; <i>L</i>-proline In ethanol; water for 16 h; Reflux; Inert atmosphere A solution of 164.2 g of methoxyphenylacetone (compound of formula IV), 244.6 g of dimethylamine hydrochloride, 90 g of paraformaldehyde and 9.9 g of a 37percent aqueous hydrochloric acid solution was dissolved in 200 mL of ethanol and 34.5 g of L - the proline and the mixed reaction were heated to reflux under nitrogen. After the reaction was refluxed for 16 hours, the mixture was cooled to room temperature. The solvent was distilled off under reduced pressure. The residue was dissolved in water and the concentrated aqueous solution was adjusted to pH And the dichloromethane was washed three times. After the organic layers were combined, the mixture was washed once with dilute aqueous ammonia, dried over anhydrous Na2S04, filtered and dried to give pale yellow oil: (S) -3-dimethylamino- 1-methoxyphenyl-1-propanone (172.6 g, molar yield 78percent, HPLC purity 98percent, ee = 95percent); used directly in the next step. 1 ^ _ESI (m / z): 222.1 (M + H) +
References: [1] Patent: CN104803861, 2017, B, . Location in patent: Paragraph 0084; 0085.
  • 3
  • [ 50-00-0 ]
  • [ 37951-49-8 ]
  • [ 124-40-3 ]
  • [ 850222-40-1 ]
YieldReaction ConditionsOperation in experiment
306.2 g With <i>L</i>-proline In ethanol at 77℃; for 36 h; In a reaction flask, add m-methoxyphenylpropan-1-one 262.4g (1.6 mol), paraformaldehyde 96g (3.2 mol), L-proline 184g (1.6 mol), dimethylamine 144g (3.2 mol), ethanol 850 ml, stirring and dissolving, heating up to 77 °C reflux reaction for 36 hours, TLC monitoring raw material is fully converted to product (developing solvent: ethyl acetate: hexane=1:3). Reaction finishes, turns on lathe does reaction solvent, adding 10percent hydrochloric acid 1300 ml dissolved, add dichloromethane 500 ml extraction three times, the organic layer for recovering raw material, the water layer is 10percent sodium hydroxide 1400 ml adjusting PH value to 10 the left and the right, adding 500 ml methylene chloride extraction three times, the combined organic layer, washed to neutral, anhydrous sodium sulfate drying, to remove the drying agent, the filtrate concentrated under reduced pressure to free until the slips away the thing, shall be the oil of 329.5g, yield 93.2percent, ee value of 97percent.
Refinement of Compound 1
The compound 1 329.5g (1.49 mol), L - dibenzoyl tartaric acid 533.4g (1.49 mol) soluble in 2966 ml in acetone, with the temperature rising to 40 °C left stirring for 24 hours, the temperature slowly drops to 5 °C the left and the right, stirring brilliantly 4h, filtering, to get the solid 810.9g. Solid soluble in 2500 ml water, 10percent NaOH to adjust the PH value to 9 - 10, by adding dichloromethane 1000 ml extraction three times, the combined organic layer, washed to neutral, anhydrous sodium sulfate drying, filtering, turns on lathe does solvent to obtain oil object 306.2g, yield 93percent. the value of the ee 99.5percent.
References: [1] Patent: CN106278915, 2017, A, . Location in patent: Paragraph 0017; 0018; 0019; 0020.
  • 4
  • [ 197145-37-2 ]
  • [ 850222-40-1 ]
References: [1] Patent: US2011/190267, 2011, A1, .
  • 5
  • [ 3027-13-2 ]
  • [ 850222-40-1 ]
References: [1] Patent: US2011/190267, 2011, A1, .
 

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