Cyclohexylamine → 4-bromo-N-cyclohexylbenzamide

HRID 1006934Notes

Reaction equation

HRID 1006934 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1>O1CCCC1>[Br:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:14])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 685154-Bromobenzoyl chloride

Product 1

HCID 7689444-bromo-N-cyclohexylbenzamideYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Cyclohexylamine (9.111 g) was dissolved in tetrahydrofuran (100 ml), followed by the addition of 4-bromobenzoyl chloride (5.04 g)/tetrahydrofuran solution (30 ml) under ice-cooling, and the mixture was stirred for 20 min. The reaction mixture was partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was recrystallized from ethyl acetate/hexane, to give the title compound as a pale pink solid (5.236 g, yield; 83%).

Workup

  1. temperaturecooling
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe resulting organic layer was washed with water
  4. dry with materialdried (over MgSO4)
  5. customevaporated
  6. customThe resulting residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c51562172c604f49af37f0ab1ed62069
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

Loading…