p-Bromoacetophenone → HCID 57849600, compound

HRID 737147Notes

Reaction equation

HRID 737147 reaction equation
[C:1]1([CH:7]2[O:12][CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=O)[CH3:21])=[CH:16][CH:15]=1>ClC(Cl)C.C(Cl)Cl>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([N:9]2[CH2:10][CH2:11][O:12][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8]2)[CH3:21])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 7466p-BromoacetophenoneHCID 911012-Phenylmorpholine

Product 1

HCID 57849600HCID 57849600, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

The above compound could be made the following way: 1 eq. of 2-Phenylmorpholine (Array) in dichloroethane could be combined with 1.2 eq. 4′-Bromoacetophenone (Aldrich) and stirred overnight at room temperature. 1.5 eq. borane-pyridine complex could be added and the reaction stirred for several hours. The reaction mixture could be diluted with methylene chloride and washed with water and brine. The organics could be dried over sodium sulfate and purified by column chromatography.

Workup

  1. addition1.5 eq. borane-pyridine complex could be added
  2. washwashed with water and brine
  3. dry with materialThe organics could be dried over sodium sulfate
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-8d03af4e86fe4103bf9523bcc40fd154
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

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