Phenethylamine → HCID 67767844, compound

HRID 361573Notes

Reaction equation

HRID 361573 reaction equation
[Cl:1][CH2:2][C:3]([N:5]1[C@@H:11]2[CH2:12][CH2:13][CH2:14][C@@H:10]2[C:9](=[O:15])[N:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]([O:26]C3C=CC=CC=3)=O)=[CH:19][CH:18]=2)[C:7]2[CH:33]=[CH:34][CH:35]=[CH:36][C:6]1=2)=[O:4].[C:37]1([CH2:43][CH2:44][NH2:45])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:1][CH2:2][C:3]([N:5]1[C@@H:11]2[CH2:12][CH2:13][CH2:14][C@@H:10]2[C:9](=[O:15])[N:8]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([NH:23][C:24]([NH:45][CH2:44][CH2:43][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:26])=[CH:21][CH:22]=2)[C:7]2[CH:33]=[CH:34][CH:35]=[CH:36][C:6]1=2)=[O:4]

Participants

5

Reactant 2

HCID 1001PhenethylamineHCID 67767539HCID 67767539, compound

Product 1

HCID 67767844HCID 67767844, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3aR*,10aS*)-4-(chloroacetyl)-9-[4-(phenoxycarbonylamino)benzyl]-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (151 mg, 0.3 mmol) in DMF (1.5 mL) was added 2-phenylethylamine (38 μl, 0.3 mmol) and the mixture was stirred at room temperature for 4 hours. This reaction mixture was diluted with ethyl acetate and washed with 2 portions of water and, then, with saturated aqueous NaCl solution. This solution was dried over NaSO4 and concentrated under reduced pressure and the residue was crystallized from ethanol-diethyl ether to provide 62 mg (yield 39%) of the title compound. m.p. 224°-226° C.

Workup

  1. washwashed with 2 portions of water
  2. dry with materialThis solution was dried over NaSO4
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was crystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-d8f6bea85bad4824bc42e7663fef1e5b
Source dataset
uspto-grants-1999_02
Patent number
US05866567

Reaction notes

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