Triethylamine → 4-Butyl-N-(6-hydroxyhexyl)benzamide

HRID 359981Notes

Reaction equation

HRID 359981 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].C(N(CC)CC)C.[CH2:16]([C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1)[CH2:17][CH2:18][CH3:19]>ClCCl>[CH2:16]([C:20]1[CH:21]=[CH:22][C:23]([C:24]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8])=[O:25])=[CH:27][CH:28]=1)[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199606-Amino-1-hexanolHCID 1200494-Butylbenzoyl chloride

Product 1

HCID 151376924-Butyl-N-(6-hydroxyhexyl)benzamideYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 23.5 g of 6-amino-1-hexanol and 30 g of triethylamine in 200 ml of dichloromethane, cooled in an ice bath, was added dropwise a solution of 43.3 g of p-butylbenzoyl chloride in 100 ml of dichloromethane. The mixture was allowed to stir at room temperature for 16 hours. Then the mixture was washed in succession with water, saturated sodium carbonate, water, and finally brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was triturated, filtered, and rinsed with cold hexane and gave 47.5 g of the desired product in 61% yield as a beige solid, m.p. 80°-81° C.

Workup

  1. washThen the mixture was washed in succession with water, saturated sodium carbonate, water, and finally brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was triturated
  5. filtrationfiltered
  6. washrinsed with cold hexane

Sources & evidence

ORD record
ord-5705c5f8eaed4d019f0e210f163fcaec
Source dataset
uspto-grants-1991_03
Patent number
US05003106

Reaction notes

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