Phenethylamine → Benzyl-4-(phenethylaminoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]-diazepin-10(1H)-one

HRID 356196Notes

Reaction equation

HRID 356196 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[C@H:13]2CCC[C@H]2[N:11]([C:19](=[O:22])[CH2:20]Br)[C:10]2[CH:23]=[CH:24][CH:25]=[CH:26][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([NH2:35])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(OCC)C>[CH2:5]([CH:6]1[CH:20]2[CH:1]([N:8]([C:14](=[O:15])[CH2:13][NH:35][CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:9]3[CH:26]=[CH:25][CH:24]=[CH:23][C:10]=3[NH:11][C:19]2=[O:22])[CH2:2][CH2:7]1)[C:4]1[CH:3]=[CH:4][CH:3]=[CH:2][CH:1]=1

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 70109710(3aR*,10aS*)-9-benzyl-4-(bromoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]-cyclopenta[e][1,4]diazepin-10(1H)-one

Product 1

HCID 86753324Benzyl-4-(phenethylaminoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]-diazepin-10(1H)-oneYield 48%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Using (3aR*,10aS*)-9-benzyl-4-bromoacetyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopent[e][1,4]-diazepin-10(1H)-one and phenethylamine, the titled compound was synthesized in substantially the same manner as in Working Example 138 in a yield of 48%, m.p. 108°-109° C. (diethyl ether).

Sources & evidence

ORD record
ord-5c6506a4346545f7a3aae45de4294e01
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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