Ammonia → 2-(1,2,3,4,10,14b-Hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)ethoxyacetamide

HRID 2260138Notes

Reaction equation

HRID 2260138 reaction equation
[CH2:1]1[CH:6]2[C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:5]2[CH2:4][CH2:3]N1CCOCC(O)=O.C([N:29]([CH2:32][CH3:33])CC)C.ClC([O:37][CH2:38][CH3:39])=O.[NH3:40].[O:41]1CCCC1>O>[CH2:1]1[CH:6]2[C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:5]2[CH2:4][CH2:3][N:40]1[CH2:39][CH2:38][O:37][CH2:33][C:32]([NH2:29])=[O:41]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 99284432-(1,2,3,4,10,14b-Hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)ethoxyacetic acid

Product 1

HCID 189997522-(1,2,3,4,10,14b-Hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)ethoxyacetamideYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.358 g of 2-(1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)ethoxyacetic acid (prepared as described in Example 2) and 0.11 g of triethylamine were added to 15 ml of tetrahydrofuran. A solution of 0.11 g of ethyl chloroformate in 2 ml of tetrahydrofuran was then added dropwise to the mixture, whilst ice-cooling, and the mixture was stirred at room temperature for 30 minutes. At the end of this time, 2 ml of 28% aqueous ammonia was added to the mixture, whilst ice-cooling, and the mixture was then stirred at room temperature for 30 minutes. The reaction mixture was then mixed with water and extracted with methylene chloride. The extract was concentrated by evaporation under reduced pressure, and the residue was subjected to column chromatography through silica gel, using 5% by volume methanol in methylene chloride as the eluent, to afford 0.29 g (yield 82%) of the title compound, melting at 66°-68° C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was then stirred at room temperature for 30 minutes
  4. extractionextracted with methylene chloride
  5. concentrationThe extract was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-2b4bfc72daf94c548aaa929ece05d2a2
Source dataset
uspto-grants-1995_12
Patent number
US05476848

Reaction notes

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