Toluene → 4-[3-(4-Methyl-1-piperazinyl)propyl]-4-azatricyclo[4.3.1.13,8]undecan-5-one

HRID 1605815Notes

Reaction equation

HRID 1605815 reaction equation
[CH:1]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:3]([NH:4][C:5]3=[O:12])[CH2:2]1)[CH2:9]2.C1(C)C=CC=CC=1.[OH-].[Na+].Br.Br.Br[CH2:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]1>O>[CH3:34][N:31]1[CH2:32][CH2:33][N:28]([CH2:27][CH2:26][CH2:25][N:4]2[C:5](=[O:12])[CH:6]3[CH2:11][CH:1]4[CH2:9][CH:8]([CH2:10][CH:3]2[CH2:2]4)[CH2:7]3)[CH2:29][CH2:30]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 2866474-Azatricyclo[4.3.1.13,8]undecan-5-oneHCID 215095401-(3-Bromopropyl)-4-methylpiperazine dihydrobromide

Product 1

HCID 543551254-[3-(4-Methyl-1-piperazinyl)propyl]-4-azatricyclo[4.3.1.13,8]undecan-5-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a well stirred solution of 2.4 gm. (0.02 mole) of 4-azatricyclo[4.3.1.13,8 ]undecan-5-one in 300 ml. of toluene, 3.2 gm. of powdered sodium hydroxide are added. After 5 minutes of vigorous stirring, 12 gm. of 1-(3-bromopropyl)-4-methylpiperazine dihydrobromide are added and the mixture heated for 20 minutes on a steam bath. The reaction mixture is cooled and stirred with 50 ml. of cold water. The toluene layer is separated, washed with 2 × 50 ml. of water and extracted with 3 × 100 ml. of 5 N HCl. The acid extracts are combined, washed with 100 ml. of ether, cooled and made basic with 2 N NaOH. The free base is extracted with 3 × 250 ml. of chloroform, dried (MgSO4) and evaporated in vacuo to give 4-[3-(4-methyl-1-piperazinyl)propyl]-4-azatricyclo[4.3.1.13,8 ]undecan-5-one.

Workup

  1. temperaturethe mixture heated for 20 minutes on a steam bath
  2. temperatureThe reaction mixture is cooled
  3. customThe toluene layer is separated
  4. washwashed with 2 × 50 ml
  5. extractionof water and extracted with 3 × 100 ml
  6. washwashed with 100 ml
  7. temperatureof ether, cooled
  8. extractionThe free base is extracted with 3 × 250 ml
  9. dry with materialof chloroform, dried (MgSO4)
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-d7ec43d12849481589318c5418fe4bec
Source dataset
uspto-grants-1976_04
Patent number
US03951950

Reaction notes

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