2'-Phenylformanilide → N-(1-Azabicyclo[3.3.0]octan-5-yl)methyl-N-formyl-2-phenylaniline

HRID 260922Notes

Reaction equation

[CH:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:2].Cl[CH2:17][C:18]12[CH2:25][CH2:24][CH2:23][N:22]1[CH2:21][CH2:20][CH2:19]2>>[N:22]12[CH2:23][CH2:24][CH2:25][C:18]1([CH2:17][N:3]([CH:1]=[O:2])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:19][CH2:20][CH2:21]2

Participants

Reactant 2

HCID 2199482'-Phenylformanilide

HCID 107732517a-(chloromethyl)-hexahydro-1H-pyrrolizine

Product 1

HCID 10781977N-(1-Azabicyclo[3.3.0]octan-5-yl)methyl-N-formyl-2-phenylaniline

Procedure

The procedures described in Example 2 were repeated except that 2-formylamino-1,1'-biphenyl (286 mg, 1.45 mmol ) and 5-chloromethyl-1-azabicyclo[3.3.0]octane (hydrochloride, 300 mg, 1.53 mmol) were employed. In this case, the desired compound was obtained as pale yellow solids (452 mg, 97.3%).

Sources & evidence

ORD record: ord-d4d371276d054992849363126a6663fc
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05530138

Reaction notes

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