Triethylamine → HCID 14547399, compound

HRID 1607514Notes

Reaction equation

HRID 1607514 reaction equation
[O:1]=[C:2]1[N:7]2[CH2:8][CH2:9][O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH:6]2[CH2:5][NH:4][CH2:3]1.C(N(CC)CC)C.[CH:24]1([C:30](Cl)=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>ClCCl>[CH:24]1([C:30]([N:4]2[CH2:3][C:2](=[O:1])[N:7]3[CH2:8][CH2:9][O:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[CH:6]3[CH2:5]2)=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 14547365HCID 14547365, compound

Product 1

HCID 14547399HCID 14547399, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Oxo-1,2,3,6,7,12b-hexahydropyrazino[1,2-d][1,4]benzoxazepine (0.9 g) and triethylamine (1 g) were dissolved in dichloromethane (20 ml), cooled in ice and cyclohexanoyl chloride (0.7 g, 1.1 equiv.) added. The mixture was stirred at room temperature for 3 h, then washed with dilute aqueous hydrochloric acid, followed by dilute aqueous ammonia solution. Evaporation of the dichloromethane gave an oil which was purified by column chromatography (SiO2 /chloroform) and crystallised from ether/40°-60° petroleum ether to give white crystals of the title compound m.p. 92°-3°;

Workup

  1. temperaturecooled in ice
  2. washwashed with dilute aqueous hydrochloric acid
  3. customEvaporation of the dichloromethane
  4. customgave an oil which
  5. customwas purified by column chromatography (SiO2 /chloroform)
  6. customcrystallised from ether/40°-60° petroleum ether

Sources & evidence

ORD record
ord-e06b0b575d704f02a24527f2ab13293a
Source dataset
uspto-grants-1989_09
Patent number
US04866056

Reaction notes

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