Triethylamine → 5-bromo-N-[2-(2-hydroxyethyl)phenyl]pentanamide

HRID 2178516Notes

Reaction equation

HRID 2178516 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10].C(N(CC)CC)C.[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24]>ClCCl>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79282o-Aminophenethyl alcoholHCID 5211735-Bromovaleryl chloride

Product 1

HCID 895005435-bromo-N-[2-(2-hydroxyethyl)phenyl]pentanamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(2-aminophenyl)ethanol a2-0 (450 g, 3.28 mol, 1 eq) and triethylamine (332 g, 3.28 mol, 1 eq) in dichloromethane (2 l) is cooled at −5° C. and bromovalerylchloride (654 g, 3.28 mol, 1 eq) in dichloromethane (2 l) is added dropwise without exceeding 0° C. The organic phase is washed with HCl 1N (4×2 l) and brine (1×2 l). The aqueous layer is extracted with dichloromethane (1×2 l). The combined organic layers are dried over MgSO4, filtered and evaporated under vacuum to afford 1008 g of 5-bromo-N-[2-(2-hydroxyethyl)phenyl]pentanamide a2-1.

Workup

  1. customwithout exceeding 0° C
  2. washThe organic phase is washed with HCl 1N (4×2 l) and brine (1×2 l)
  3. extractionThe aqueous layer is extracted with dichloromethane (1×2 l)
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-aaaf43f159034b19ab4a434652d2401a
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

Loading…