4-(Bromoacetyl)benzonitrile → HCID 58374171, compound

HRID 1948486Notes

Reaction equation

HRID 1948486 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@H:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]1.Br[CH2:13][C:14]([C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1)=[O:15]>C1(C)C=CC=CC=1>[C:20]([C:19]1[CH:22]=[CH:23][C:16]([C:14](=[O:15])[CH2:13][N:1]2[CH2:6][CH2:5][CH2:4][C@H:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]2)=[CH:17][CH:18]=1)#[N:21]

Participants

4

Reactant 2

HCID 986544-(Bromoacetyl)benzonitrileHCID 187784Ethyl (3S)-piperidine-3-carboxylate

Product 1

HCID 58374171HCID 58374171, compoundYield 125.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of (S)-ethyl piperidine-3-carboxylate (5 g, 31.8 mmol) in toluene (50 mL) was added 4-(2-bromoacetyl)benzonitrile (7.84 g, 35.0 mmol). The reaction mixture was stirred for 48 hours. The reaction mixture was concentrated in vacuo to yield 12 g of a yellow solid which was purified by triturating in EtOAc. The solid material was collected and washed with EtOAc then dried in vacuo to give 6 g of (S)-ethyl 1-(2-(4-cyanophenyl)-2-oxoethyl)piperidine-3-carboxylate, hydrobromide. MS (m+1)=301. HPLC Peak RT=1.57 minutes (Analytical Method B).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-820485dc668348ccaaab500b912d1684
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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