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[ CAS No. 894769-77-8 ]

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2D
Chemical Structure| 894769-77-8
Chemical Structure| 894769-77-8
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Product Details of [ 894769-77-8 ]

CAS No. :894769-77-8MDL No. :MFCD11849799
Formula : C18H23FN2O2 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :318.39Pubchem ID :69122176
Synonyms :

Computed Properties of [ 894769-77-8 ]

TPSA : 53.3 H-Bond Acceptor Count : 4
XLogP3 : 3.2 H-Bond Donor Count : 0
SP3 : 0.56 Rotatable Bond Count : 4

Safety of [ 894769-77-8 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P280-P305+P351+P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 894769-77-8 ]

  • Upstream synthesis route of [ 894769-77-8 ]

[ 894769-77-8 ] Synthesis Path-Upstream   1~2

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  • [ 894769-77-8 ]
YieldReaction ConditionsOperation in experiment
50%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 20℃;
Stage #2: at -78℃; for 4 h;
Step-1:
4-Cyano-4-(4-fluoro-benzyl)-piperidine-1-carboxylic acid tert butyl ester
To a solution of diisopropylamine (3.2 ml, 22.8 mmol) in THF was added a solution of n-butyl lithium in hexane (1.6M, 15.8 ml, 26.6 mmol) at 0° C.
The reaction mixture was stirred at room temperature for 1 hour then cooled to -78° C. A solution of 4-cyano-1-boc piperidine (4.0 g, 19 mmol) in THF was then added drop wise at -78° C. and the mixture was allowed to -40° C. over a period of 1 hour.
The mixture was recooled to -78° C. and a solution of 4-fluorobenzyl bromide in THF was added drop wise.
The reaction mixture was stirred at -78° C. for 4 hours then quenched at 0° C. with a saturated aqueous solution of ammonium chloride.
The product was extracted with ethyl acetate.
The organic layer was washed with brine solution, dried over sodium sulfate and concentrated.
The crude product was crystallized from hexane to afford 3 g (50percent) of 4-Cyano-4-(4-fluoro-benzyl)-piperidine-1-carboxylic acid tert butyl ester. LC/MS [M+H]+: 319.4
49.6%
Stage #1: With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78 - -40℃; Cooling with ice
Stage #2: at -78℃;
Step-1: 4-Cyano-4-(4-fluoro-benzyl)-piperidine-1-carboxylic acid tent butyl ester; 1.6 (M) solution n-butyl lithium in hexane (15.8 ml, 26.6 mmol) was added to an ice-chilled solution of diisopropylamine (3.2 ml, 22.8 mmol) in THF. The resulting mixture was stirred at room temperature for 1 hour. The solution was then cooled to -78° C. and a solution of 4-cyano-1-boc piperidine (4.0 g, 19 mmol) in THF was added dropwise. The mixture was warmed to -40° C. over a period of 1 hour, then cooled to -78° C. A solution of 4-fluorobenzyl bromide in THF was added dropwise and the resuling mixture was stirred at -78° C. for 4 hours then quenched at 0° C. by the addition of saturated aqueous solution of ammonium chloride. The product was extracted with ethyl acetate. The organic layer was washed with brine solution and dried over sodium sulfate. The organic layer was concentrated and the crude mass was crystallized from hexane to afford 3 g (49.6percent) of 4-cyano-4-(4-fluoro-benzyl)-piperidine-1-carboxylic acid tert butyl ester. LC/MS [M+H]+: 319.4
Reference: [1] Patent: US2010/168080, 2010, A1, . Location in patent: Page/Page column 48-49
[2] Patent: US2010/152160, 2010, A1, . Location in patent: Page/Page column 31
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Reference: [1] Patent: WO2006/66948, 2006, A1, . Location in patent: Page/Page column 68
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