Phenylacetyl chloride → N-(1-[9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl]-4-piperidyl)-2-phenylacetamide

HRID 258294Notes

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.[C:24]1([CH2:30][C:31](Cl)=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH:21]1[C:22]2[C:9]3([CH2:8][N:5]4[CH2:6][CH2:7][CH:2]([NH:1][C:31](=[O:32])[CH2:30][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[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

Reactant 2

HCID 7679Phenylacetyl chloride

HCID 193810314-Amino-1-(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)piperidine

Product 1

HCID 19381088N-(1-[9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl]-4-piperidyl)-2-phenylacetamide

Procedure

Using a procedure similar to that described in Example 27 except starting with 4-amino-1-[9,10-dihydro-9,10-methanoanthracen-9-ylmethyl]piperidine (described in Example 8b) and phenylacetyl chloride, the title compound was obtained as a white solid (70%), mp 199.8°-202.1° C.; MS(CI): 423 (M+H); NMR (300 MHz,DMSO-d6): 1.37(m, 2H), 1.67(m, 2H), 2.26(m, 2H), 2.45(s, 2H), 2.93(m, 2H), 3.36(s, 2H), 3.53(m, 1H), 4.30(s, 1H), 6.91(m, 4H), 7.17-7.28(m, 9H), 7.95(d, 1H, J=8.4 Hz).

Sources & evidence

ORD record: ord-058ed389e1af4e30a483c49dbbc22727
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05266570

Reaction notes

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