2-Bromoethanol → HCID 86602703, compound

HRID 1375045Notes

Reaction equation

HRID 1375045 reaction equation
Br[CH2:2][CH2:3][OH:4].[F:5][C:6]([F:37])([F:36])[C:7]1[CH:8]=[C:9]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[C:10]([N:12]1[CH2:17][CH2:16][NH:15][CH2:14][C@H:13]1[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1)=[O:11]>C(#N)C>[F:37][C:6]([F:5])([F:36])[C:7]1[CH:8]=[C:9]([CH:29]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:31]=1)[C:10]([N:12]1[CH2:17][CH2:16][N:15]([CH2:2][CH2:3][OH:4])[CH2:14][C@H:13]1[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1)=[O:11]

Participants

4

Reactant 2

HCID 108982-BromoethanolHCID 53868920HCID 53868920, compound

Product 1

HCID 86602703HCID 86602703, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

2-Bromoethanol (310 mg) was added to a solution of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-[4-(trifluoromethyl)-benzyl]piperazine (1 g) in acetonitrile (10 ml). The reaction mixture was stirred at 70° C. for 19 hours. The mixture was filtered, and the residue on filter was washed with dichloromethane twice. The filtrate and combined washings were concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with methanol in dichloromethane (2% then 5%) to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-(2-hydroxyethyl)-2-[4-(trifluoromethyl)benzyl]piperazine (927 mg) as an amorphous powder.

Workup

  1. filtrationThe mixture was filtered
  2. filtrationthe residue on filter
  3. washwas washed with dichloromethane twice
  4. concentrationwere concentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluted with methanol in dichloromethane (2%

Sources & evidence

ORD record
ord-0c5b75a7d1f049c4a6664d4581cce35f
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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