4-(Bromoacetyl)benzonitrile → (R)-ethyl 2-(1-(2-(4-cyanophenyl)-2-oxoethyl)piperidin-3-yl)acetate

HRID 1948490Notes

Reaction equation

HRID 1948490 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=[O:4].[NH:13]1[CH2:18][CH2:17][CH2:16][C@H:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14]1>C1(C)C=CC=CC=1>[C:9]([C:8]1[CH:11]=[CH:12][C:5]([C:3](=[O:4])[CH2:2][N:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14]2)=[CH:6][CH:7]=1)#[N:10]

Participants

4

Reactant 2

HCID 986544-(Bromoacetyl)benzonitrileHCID 7161133ethyl 2-[(3R)-piperidin-3-yl]acetate

Product 1

HCID 58374115(R)-ethyl 2-(1-(2-(4-cyanophenyl)-2-oxoethyl)piperidin-3-yl)acetateYield 68.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 4-(2-bromoacetyl)benzonitrile (5.5g, 24.55 mmol) in toluene was added (R)-ethyl 2-(piperidin-3-yl)acetate (4 g, 23.36 mmol). The reaction mixture was stirred for 4 days at room temperature and then stirred from one day at 50° C. Solvents were removed in vacuo. The resulting solids were triturated with EtOAc. The solid material was filtered and washed with EtOAc. The solid material was collected and dried to yield 5 g of (R)-ethyl 2-(1-(2-(4-cyanophenyl)-2-oxoethyl)piperidin-3-yl)acetate. MS (M+1)=314. HPLC Peak RT=0.77 minutes.

Workup

  1. stirringstirred from one day at 50° C
  2. customSolvents were removed in vacuo
  3. customThe resulting solids were triturated with EtOAc
  4. filtrationThe solid material was filtered
  5. washwashed with EtOAc
  6. customThe solid material was collected
  7. customdried

Sources & evidence

ORD record
ord-8dce0bb7f8e54713a7240acfeed0ccf8
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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