Benzenepropanoyl chloride → N-(1-[9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl]-4-piperidyl)-3-phenylpropionamide

HRID 258292Notes

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][CH2:31][C:32](Cl)=[O:33])[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:32](=[O:33])[CH2:31][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 64801Benzenepropanoyl chloride

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

Product 1

HCID 19381101N-(1-[9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl]-4-piperidyl)-3-phenylpropionamide

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 3-phenylpropionyl chloride, the title compound was obtained as a white solid (46%) by crystallization from ether-ethyl acetate, mp 149.0°-50.0° C.; MS(CI): 437 (M+H); NMR (300 Hz, DMSO-d6): 1.20-1.40(m, 2H), 1.55-1.69(m, 2H), 2.17-2.40(m, 4H), 2.44(s, 2H), 2.79(t, 2H, J=8.1 Hz), 2.85-2.98(m, 2H), 3.33(m, 2H), 3.53(m, 1H), 4.30(s, 1H), 6.85-6.98(m, 4H), 7.10-7.32(m, 9H), 7.66(d, 1H, J=7.5 Hz).

Sources & evidence

ORD record: ord-c70cd9e5f2d44fb490ae02e08b0edb89
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05266570

Reaction notes

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