Oxalyl chloride → 5-(4'-Acetamido-2'-methylbiphenyl-4-carbonyl)-1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]

HRID 1870906Notes

Reaction equation

HRID 1870906 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([OH:19])=O)=[CH:13][CH:12]=2)=[C:7]([CH3:20])[CH:6]=1)(=[O:3])[CH3:2].[CH3:21][N:22]1[CH2:27][CH2:26][C:25]2([C:38]3[C:30](=[CH:31][C:32]4[CH2:33][CH2:34][NH:35][C:36]=4[CH:37]=3)[O:29][CH2:28]2)[CH2:24][CH2:23]1.C(Cl)(=O)C(Cl)=O>>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([N:35]3[C:36]4[CH:37]=[C:38]5[C:25]6([CH2:28][O:29][C:30]5=[CH:31][C:32]=4[CH2:33][CH2:34]3)[CH2:26][CH2:27][N:22]([CH3:21])[CH2:23][CH2:24]6)=[O:19])=[CH:15][CH:16]=2)=[C:7]([CH3:20])[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 106579521'-Methyl-6,7-dihydro-2H,5H-spiro[furo[2,3-f]indole-3,4'-piperidine]HCID 186942634'-Acetamido-2'-methylbiphenyl-4-carboxylic acid

Product 1

HCID 186943005-(4'-Acetamido-2'-methylbiphenyl-4-carbonyl)-1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]Yield 43%

Procedure

The title compound was prepared from 4'-acetamido-2'-methylbiphenyl-4-carboxylic acid (D13) and 1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidinel (D7) using oxalyl chloride to give the title compound as a yellow oil (43%). This was converted to its oxalate salt which crystallised as a white solid from acetone.

Sources & evidence

ORD record
ord-d57b74b64677458b9daec536ac0609c8
Source dataset
uspto-grants-2000_08
Patent number
US06100272

Reaction notes

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