Piperazine → Norchlorcyclizine

HRID 1406665Notes

Reaction equation

HRID 1406665 reaction equation
Cl[CH:2]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>C1COCC1>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([CH:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 2415844-Chlorobenzhydryl chloride

Product 1

HCID 9340Norchlorcyclizine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to General Procedure A: chloro(4-chlorophenyl)phenylmethane (4{26}, 5 mL, 26.1 mmol, 1 equiv.), piperazine (13.5 g, 156.7 mmol, 6 equiv.), THF (57.0 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{26} (6.34 g, 85%) as a yellow liquid. 1H-NMR (500 MHz, CDCl3): δ 7.39-7.37 (m, 4H), 7.30-7.24 (m, 4H) 7.20 (t, 1H, J=7.5 Hz), 4.21 (s, 1H), 2.89 (t, 4H, J=5.0 Hz), 2.36 (br s, 4H), 1.82 (br s, 1H). 13C-NMR (125 MHz, CDCl3): δ 142.0, 141.2, 132.4, 129.2, 128.5, 128.5, 127.8, 127.0, 75.9, 53.2, 46.2.

Workup

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (4:1 EtOAc:MeOH)
  3. customafforded 5{26} (6.34 g, 85%) as a yellow liquid

Sources & evidence

ORD record
ord-4ec6345129a44d47893c37c0e9112cd8
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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