Water → HCID 19838251, compound

HRID 1381621Notes

Reaction equation

HRID 1381621 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH2:28][CH2:29][NH2:30])[CH:23]=[CH:24][C:25]=1[O:26][CH3:27].O>ClCCl>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH2:28][CH2:29][NH:30][C:15](=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:23]=[CH:24][C:25]=1[O:26][CH3:27]

Participants

5

Reactant 3

HCID 962WaterHCID 8421HomoveratrylamineHCID 32922159-Phenylnonanoic acid

Product 1

HCID 19838251HCID 19838251, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 9-phenylnonanoic acid (1.934 g) and N,N'-carbonyldiimidazole (1.34 g) in dry dichloromethane (20 ml) was stirred at 20° for one hour and a solution of 3,4-dimethoxybenzeneethanamine (1.4 ml) in dry dichloromethane (10 ml) then added. The mixture was stirred at 20° for 18 hours and water added. The organic phase was separated, washed with dilute hydrochloric acid, aqueous sodium bicarbonate and brine, dried over magnesium sulphate and evaporated to leave a solid. Crystallisation from 2-propanol gave the amide as colourless prisms (2.7 g); mp, 117°-119°.

Workup

  1. customThe organic phase was separated
  2. washwashed with dilute hydrochloric acid, aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customto leave a solid
  6. customCrystallisation from 2-propanol

Sources & evidence

ORD record
ord-0c75cddf73144bcaa86074be2f3c1503
Source dataset
uspto-grants-1989_02
Patent number
US04803225

Reaction notes

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