3,5-Di-tert-butyl-4-hydroxybenzoyl chloride → HCID 14300313, compound

HRID 1761846Notes

Reaction equation

HRID 1761846 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8](Cl)=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH2:19]([O:26][C:27]([N:29]1[CH2:35][CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C>[OH:14][C:13]1[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]([C:8]([N:32]2[CH2:33][CH2:34][CH2:35][N:29]([C:27]([O:26][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:28])[CH2:30][CH2:31]2)=[O:9])=[CH:11][C:12]=1[C:15]([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chlorideHCID 4384955Benzyl 1,4-diazepane-1-carboxylate

Product 1

HCID 14300313HCID 14300313, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 13.4 g (0.05 mol) of 3,5-di-tert.-butyl-4-hydroxybenzoyl chloride and 12.4 g (0.053 mol) of 1-benzyloxycarbonylhomopiperazine in 200 ml of acetonitrile is heated under reflux, with stirring, for 6 hour. The solvent is then removed by distillation under reduced pressure, the residue is partitioned between methylene chloride and dilute hydrochloric acid, and the organic phase is separated off and washed with saturated brine. After drying over sodium sulfate and removal of the solvent by distillation under reduced pressure, the crystalline residue is digested with hot diisopropyl ether, filtered off with suction, washed with diisopropyl ether and dried.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. customThe solvent is then removed by distillation under reduced pressure
  4. customthe residue is partitioned between methylene chloride and dilute hydrochloric acid
  5. customthe organic phase is separated off
  6. washwashed with saturated brine
  7. dry with materialAfter drying over sodium sulfate and removal of the solvent by distillation under reduced pressure
  8. filtrationfiltered off with suction
  9. washwashed with diisopropyl ether
  10. customdried

Sources & evidence

ORD record
ord-adf67d0c2e6d4c239ebb395b912a1ae6
Source dataset
uspto-grants-1989_05
Patent number
US04829061

Reaction notes

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