1-Methylpiperazine → 1-(N,N-Dioctadecylcarbamyl)-4-Methylpiperazine

HRID 371789Notes

Reaction equation

HRID 371789 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:8]([N:26]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[C:27](Cl)=[O:28])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C1C=CC=CC=1>[CH2:8]([N:26]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[C:27]([N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)=[O:28])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 3016265N,N-dioctadecylcarbamoyl chloride

Product 1

HCID 204329951-(N,N-Dioctadecylcarbamyl)-4-Methylpiperazine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1-methylpiperazine (5 ml.), N,N-dioctadecylcarbamylchloride (5.0 g.) and benzene (50 ml.) is refluxed and stirred for three hours. The white precipitate of 1-methylpiperazine hydrochloride is removed by filtration and the filtrate concentrated in vacuo to a yellow oil (4.5 g.). The oil is then charged on a silica gel pad and eluted with benzene in 50 ml. fractions. Fractions 10-15 are combined, a large volume of methanol added and the white crystalline material which separates filtered and dried, m.p. 46°-47° C. (1.45 g.).

Workup

  1. temperatureis refluxed
  2. customThe white precipitate of 1-methylpiperazine hydrochloride is removed by filtration
  3. concentrationthe filtrate concentrated in vacuo to a yellow oil (4.5 g.)
  4. additionThe oil is then charged on a silica gel pad
  5. washeluted with benzene in 50 ml
  6. additiona large volume of methanol added
  7. filtrationthe white crystalline material which separates filtered
  8. customdried

Sources & evidence

ORD record
ord-13b7f6059107404fa9ca739afa80fcd4
Source dataset
uspto-grants-1978_05
Patent number
US04087552

Reaction notes

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