Potassium Carbonate → 5-(N,N-Dibenzylglycyl)-2-(heptyloxy)benzamide

HRID 1974217Notes

Reaction equation

HRID 1974217 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([N:14]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:15][C:16]([C:18]1[CH:26]=[C:22]([C:23]([NH2:25])=[O:24])[C:21]([OH:27])=[CH:20][CH:19]=1)=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.I[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>CC(=O)CC>[CH2:28]([N:14]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:15][C:16]([C:18]1[CH:19]=[CH:20][C:21]([O:27][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[C:22]([CH:26]=1)[C:23]([NH2:25])=[O:24])=[O:17])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 202741-IodoheptaneHCID 1217275-((Bis(benzyl)amino)acetyl)salicylamide

Product 1

HCID 214888895-(N,N-Dibenzylglycyl)-2-(heptyloxy)benzamideYield 99.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of potassium carbonate (3.73 g), 5-(N,N-dibenzylglycyl) salicylamide (10 g) and 1-iodo heptane (7.5 g) in butanone (200 ml) was stirred and heated under reflux for 24 hours. The solid was filtered off and the filtrate was evaporated. The residue was partitioned between ethyl acetate and water. The dried (MgSO4) ethyl acetate solution was evaporated to give a yellow oil (12.6 g) which crystallised twice from isopropanol to yield the ether (6.3 g) m.p. 97.5°-98°.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 24 hours
  3. filtrationThe solid was filtered off
  4. customthe filtrate was evaporated
  5. customThe residue was partitioned between ethyl acetate and water
  6. dry with materialThe dried (MgSO4) ethyl acetate solution
  7. customwas evaporated

Sources & evidence

ORD record
ord-eded272c926b42ee9a7bfb331ade1567
Source dataset
uspto-grants-1976_12
Patent number
US04000192

Reaction notes

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