(3-Bromo-4-((5-phenylpentyl)amino)phenyl)methanol → 3-Bromo-4-((5-phenylpentyl)amino)benzaldehyde

HRID 400353Notes

Reaction equation

HRID 400353 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:20][OH:21])[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH:20]=[O:21]

Participants

4

Reactant 2

HCID 86687855(3-Bromo-4-((5-phenylpentyl)amino)phenyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 866878543-Bromo-4-((5-phenylpentyl)amino)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-bromopentylbenzene [14469-83-1](4 g, 17.6 mmol) in HMPA (55 g) was treated with 4-amino-3-bromobenzemethanol [146019-46-7] and dry K2CO3 (4.87 g, 35.2 mmol) for ˜18 h at 120° C. The mixture was cooled to rt, poured onto water (600 mL) and extracted with ethyl acetate (200 mL). The organic phase was washed with water (200 mL), dried over Na2SO4, concentrated, and purified by chromatography (ethyl acetate/hexane) to give (3-bromo-4-((5-phenylpentyl)amino)phenyl)methanol (2.24 g, 37%). A solution of (3-bromo-4-((5-phenylpentyl)amino)phenyl)methanol (8.0 g, 23 mmol) in dichloromethane (160 mL) was treated with silica gel (24 g) and PCC (14.9 g, 69 mmol) at rt for ˜18 h. The mixture was concentrated, and purified by chromatography on silica gel (ethyl acetate-hexane) to give 3-bromo-4-((5-phenylpentyl)amino)benzaldehyde Intermediate-21 (3.5 g, 44%).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by chromatography on silica gel (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-82544e20936a497e90e496fc7c700a7c
Source dataset
uspto-grants-2014_06
Patent number
US08741875B2

Reaction notes

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