1-Methyl-4-(piperidin-4-yl)piperazine → 1-Methyl-4-[1-(2-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-piperidin-4-yl]-piperazine

HRID 1041175Notes

Reaction equation

HRID 1041175 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9][C:8]=2[CH:15]=1)([O-:3])=[O:2].[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:19][CH2:18]1>>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([CH:23]2[CH2:28][CH2:27][N:26]([CH:11]3[CH2:10][CH2:9][C:8]4[CH:15]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=4[CH2:13][CH2:12]3)[CH2:25][CH2:24]2)[CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 7957071-Methyl-4-(piperidin-4-yl)piperazineHCID 457903192-Nitro-8,9-dihydro-5H-benzo[7]annulen-7(6H)-one

Product 1

HCID 672643851-Methyl-4-[1-(2-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-piperidin-4-yl]-piperazine

Procedure

1-Methyl-4-[1-(2-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-piperidin-4-yl]-piperazine was prepared from 2-nitro-5,6,8,9-tetrahydrobenzocyclohepten-7-one and 1-methyl-4-piperidin-4-yl-piperazine in an analogous manner to Example 178a. Product was isolated as a tan solid. 1H NMR (CDCl3, 400 MHz) δ 7.98 (s, 1H), 7.97 (d, 1H, J=8.08 Hz), 7.24 (d, 1H, J=8.08 Hz), 2.95 (dd, 2H, J=7.32, 12 Hz), 2.84 (d, 2H, J=12 Hz), 2.74 (m, 3H), 2.60 (broad s, 4H), 2.47 (m, 3H), 2.29 (s, 5H), 2.11 (m, 2H), 1.82 (d, 2H, J=12 Hz), 1.67 (m, 2H), 1.54 (m, 2H), 1.40 (m, 2H).

Workup

  1. customProduct was isolated as a tan solid

Sources & evidence

ORD record
ord-54243fae19604ce4a12d938b0e4a3575
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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