2-Bromo-N-(4-methylphenyl)acetamide → HCID 86655289, compound

HRID 2192372Notes

Reaction equation

HRID 2192372 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]([C:12]1([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2.[Br:25][CH2:26][C:27]([NH:29][C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1)=[O:28]>C(#N)C>[Br-:25].[C:19]1([C:12]2([C:10]([O:9][C@@H:3]3[CH:4]4[CH2:7][CH2:8][N+:1]([CH2:26][C:27](=[O:28])[NH:29][C:30]5[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=5)([CH2:6][CH2:5]4)[CH2:2]3)=[O:11])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 947222-Bromo-N-(4-methylphenyl)acetamideHCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Product 1

HCID 86655289HCID 86655289, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (51 mg) in acetonitrile (1 mL) was added 2-bromo-N-p-tolyl-acetamide (Example 46a) (39 mg). The reaction was stirred at room temperature overnight and the acetonitrile was removed under reduced pressure. The material was recrystallised from acetonitrile/ethyl acetate to afford the title compound as a colourless solid (16 mg).

Workup

  1. customthe acetonitrile was removed under reduced pressure
  2. customThe material was recrystallised from acetonitrile/ethyl acetate

Sources & evidence

ORD record
ord-7c0b8b639443472f852e934b36b3dfb2
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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