Triphenylphosphine dibromide → 4-[N-(7-Bromo-5-oxahept-1-yl)-N-(isopropyl)amino]-1-benzylpiperidine

HRID 1181524Notes

Reaction equation

HRID 1181524 reaction equation
O[CH2:2][CH2:3][O:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1)[CH:10]([CH3:12])[CH3:11].[Br:26]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>ClCCl>[Br:26][CH2:2][CH2:3][O:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1)[CH:10]([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 70579Triphenylphosphine dibromideHCID 674286734-[N-(7-Hydroxy-5-oxahept-1-yl)-N-(isopropyl)amino]-1-benzylpiperidine

Product 1

HCID 674276244-[N-(7-Bromo-5-oxahept-1-yl)-N-(isopropyl)amino]-1-benzylpiperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[N-(7-Hydroxy-5-oxahept-1-yl)-N-(isopropyl)amino]-1-benzylpiperidine (2.0 g, 5.7 mmol) was treated with dibromotriphenylphosphorane (6.1 g, 14.4 mmol) in dichloromethane for 2 h. The reaction mixture was then was washed with 1 N sodium hydroxide, saturated sodium bicarbonate, brine, dried over magnesium sulfate and concentrated to give the title intermediate, which was used without further purification.

Workup

  1. washThe reaction mixture was then was washed with 1 N sodium hydroxide, saturated sodium bicarbonate, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-247cbcde0c884e119d0dd42cba91502e
Source dataset
uspto-grants-2007_10
Patent number
US07285564B2

Reaction notes

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