Phenethylamine → HCID 67767615, compound

HRID 361572Notes

Reaction equation

HRID 361572 reaction equation
O([C:8]([NH:10][C:11]1[CH:32]=[CH:31][C:14]([CH2:15][N:16]2[C:22](=[O:23])[C@H:21]3[CH2:24][CH2:25][CH2:26][C@H:20]3[NH:19][C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]2=3)=[CH:13][CH:12]=1)=[O:9])C1C=CC=CC=1.[CH2:33](CN)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[CH3:42][N:43](C=O)C>C(OCC)(=O)C>[CH2:33]([N:43]([CH3:42])[C:8](=[O:9])[NH:10][C:11]1[CH:32]=[CH:31][C:14]([CH2:15][N:16]2[C:22](=[O:23])[C@H:21]3[CH2:24][CH2:25][CH2:26][C@H:20]3[NH:19][C:18]3[CH:27]=[CH:28][CH:29]=[CH:30][C:17]2=3)=[CH:13][CH:12]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 6228DimethylformamideHCID 67767670HCID 67767670, compound

Product 1

HCID 67767615HCID 67767615, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3aR*,10aS*)-9-[4-(phenoxycarbonylamino)benzyl]-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (0.43 g, 1 mmol) in DMF (5 mL) was added N-benzylmethylamine (0.14 mL, 1.1 mmol) and the mixture was stirred at room temperature for 84 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 MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1) to provide 0.30 g (yield 66%) of the title compound. Amorphous.

Workup

  1. washwashed with 2 portions of water
  2. dry with materialThis solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1)

Sources & evidence

ORD record
ord-3a8f6c8592b44aadb1c7153bc788c097
Source dataset
uspto-grants-1999_02
Patent number
US05866567

Reaction notes

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