Triethylamine → HCID 14547399, compound

HRID 543131Notes

Reaction equation

HRID 543131 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-78907bae9d8040f1a2b7e2aa66b56276
Source dataset
uspto-grants-1987_04
Patent number
US04661489

Reaction notes

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