1-(3,4-Dichlorophenyl)piperazine → HCID 10431149, compound

HRID 887196Notes

Reaction equation

HRID 887196 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[N:15]([C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][N:22]=[CH:23]2)=[C:16]=[O:17]>C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][N:12]([C:16]([NH:15][C:18]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:19]=3[CH:20]=[CH:21][N:22]=[CH:23]4)=[O:17])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 936011-(3,4-Dichlorophenyl)piperazineHCID 115863575-Isocyanatoisoquinoline

Product 1

HCID 10431149HCID 10431149, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-(3,4-Dichlorophenyl)piperazine (1280 mg, 5.55 mmol) in diethyl ether (30 mL) was treated with the product from Example 61A (˜40 mL). The mixture was filtered, the filter cake washed with diethyl ether, and dried under reduced pressure to provide the title compound as a white solid (1.78 g, 80%). 1H NMR (300 MHz, DMSO-d6) δ 9.29 (d, J=1.0 Hz, 1H), 8.84 (s, 1H), 8.49 (d, J=5.8 Hz, 1H), 7.92 (d, J=7.8 Hz, 1H), 7.78 (m, 1H), 7.61-7.71 (m, 2H), 7.44 (d, J=8.8 Hz, 1H), 7.22 (d, J=3.1 Hz, 1H), 7.01 (dd, J=9.1, 2.7 Hz, 1H), 3.68 (m, 4H), 3.30 (m, 4H); MS (ESI+) m/z 401/403 (M+H+, 35Cl/37Cl).

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter cake washed with diethyl ether
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-f63f9a66786f4cd382c2edd747ec93ea
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

Loading…