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

HRID 2209593Notes

Reaction equation

HRID 2209593 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](Cl)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26]>>[CH:21]1[C:22]2[C:9]3([CH2:8][N:5]4[CH2:6][CH2:7][CH:2]([NH:1][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[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 62493Pivaloyl chlorideHCID 193810314-Amino-1-(9,10-dihydro-9,10-methanoanthracen-9-ylmethyl)piperidine

Product 1

HCID 19381095N-(1-[9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl]-4-piperidyl)-2,2-dimethylpropionamide

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 and pivaloyl chloride, the title compound was obtained as a white solid (87%), mp 181.5°-2.5° C.; MS(CI): 389 (M+H); NMR (300 MHz,DMSO-d6): 1.05(s, 9H), 1.37-1.66(m, 4H), 2.24(m, 2H), 2.45(s, 2H), 2.97(m, 2H), 3.31(s, 2H), 3.56(m, 1H), 4.30(s, 1H), 6.91(m, 4H), 7.06(d, 1H, J=8.1 Hz), 7.17-7.27(m, 4H).

Sources & evidence

ORD record
ord-f8b5830766294d1896c2354c871175c1
Source dataset
uspto-grants-1995_10
Patent number
US05455246

Reaction notes

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