4-(Bromoacetyl)benzonitrile → HCID 86656387, compound

HRID 1948484Notes

Reaction equation

HRID 1948484 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:12][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>[BrH:12].[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 86656387HCID 86656387, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of commercially available (S)-ethyl piperidine-3-carboxylate (10 g, 63.6 mmol) in 200 mL toluene was added 4-(2-bromoacetyl)benzonitrile (17 g, 76 mmol). The reaction mixture was stirred overnight. The next day, the precipitated solid was collected by filtration and washed with ethyl acetate (×3) and dried under vacuum to give 15.2 g of (S)-ethyl 1-(2-(4-cyanophenyl)-2-oxoethyl)piperidine-3-carboxylate hydrobromide. MS (M+1)=301. HPLC Peak RT=1.51 minutes.

Workup

  1. filtrationThe next day, the precipitated solid was collected by filtration
  2. washwashed with ethyl acetate (×3)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-290d4d68e7074ba88f8e0efc351fbfd5
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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