1-(3-Chlorophenyl)piperazine monohydrochloride → 8-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyloxy]-8-azaspiro[4.5]decan-7,9-dione hydrochloride hemihydrate

HRID 868549Notes

Reaction equation

HRID 868549 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][N:6]1[C:15](=[O:16])[CH2:14][C:9]2([CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:8][C:7]1=[O:17].[ClH:18].[Cl:19][C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1>CCN(CC)CC>[OH2:5].[ClH:19].[Cl:19][C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][CH2:4][O:5][N:6]3[C:15](=[O:16])[CH2:14][C:9]4([CH2:13][CH2:12][CH2:11][CH2:10]4)[CH2:8][C:7]3=[O:17])[CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1.[Cl:19][C:20]1[CH:21]=[C:22]([N:26]2[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][CH2:4][O:5][N:6]3[C:15](=[O:16])[CH2:14][C:9]4([CH2:13][CH2:12][CH2:11][CH2:10]4)[CH2:8][C:7]3=[O:17])[CH2:28][CH2:27]2)[CH:23]=[CH:24][CH:25]=1.[ClH:18]

Participants

4

Reactant 2

HCID 256811-(3-Chlorophenyl)piperazine monohydrochlorideHCID 142805838-(3-Bromopropyloxy)-8-azaspiro[4.5]decan-7,9-dione

Product 1

HCID 1317157328-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyloxy]-8-azaspiro[4.5]decan-7,9-dione hydrochloride hemihydrate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 8-(3-bromopropyloxy)-8-azaspiro[4.5]decan-7,9-dione (4.0 g) and 1-(3-chlorophenyl)piperazine hydrochloride (3.06 g) in 50 ml of Et3N was heated to reflux with stirring under N2. After 1 hour TLC (thin layer chromatography) showed the absence of starting material. The excess Et3N was removed in vacuo and the residue chromatographed on silica using ethyl acetate as the eluent. Fractions containing the desired product were combined and concentrated in vacuo.

Workup

  1. temperatureto reflux
  2. customThe excess Et3N was removed in vacuo
  3. customthe residue chromatographed on silica
  4. additionFractions containing the desired product
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ba4e93a36a248379f4efa5efff7e99b
Source dataset
uspto-grants-1988_10
Patent number
US04780466

Reaction notes

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