o-Chlorophenylacetic acid → N-(1-[9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl]-4-piperidyl)-2-(2-chlorophenyl)acetamide

HRID 258298Notes

Reaction equation

HRID 258298 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]23[CH2:23][CH:16]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=42)[C:15]2[C:10]3=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:4][CH2:3]1.[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][C:32](O)=[O:33]>>[CH:21]1[C:22]2[C:9]3([CH2:8][N:5]4[CH2:6][CH2:7][CH:2]([NH:1][C:32](=[O:33])[CH2:31][C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=5[Cl:24])[CH2:3][CH2:4]4)[CH2:23][CH:16]([C:15]4[C:10]3=[CH:11][CH:12]=[CH:13][CH:14]=4)[C:17]=2[CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 17124o-Chlorophenylacetic acidHCID 193810314-Amino-1-(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)piperidine

Product 1

HCID 19380981N-(1-[9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl]-4-piperidyl)-2-(2-chlorophenyl)acetamide

Procedure

Using a procedure similar to that described in Example 6 except starting with 4-amino-1-[9,10-dihydro-9,10-methanoanthracen-9-ylmethyl]piperidine and 2-chlorophenylacetic acid, the title compound was obtained as a pink solid (71%), mp 212.0°-14.0° C.; MS(CI): 457 (M+H); NMR (300 MHz,DMSO-d6): 1.38(m, 2H), 1.70(m, 2H), 2.28(m, 2H), 2.46(s, 2H), 2.93(m, 2H), 3.30(m,submerged, 2H), 3.54(m, 3H), 4.31(s, 1H), 6.87-6.96(m, 4H), 7.17-7.41(m, 8H), 7.96(d, 1H, J=7.7 Hz).

Sources & evidence

ORD record
ord-a17f610e32c6463d8d8e98798647dd84
Source dataset
uspto-grants-1993_11
Patent number
US05266570

Reaction notes

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