1-Methylpiperazine → 90053-70-6

HRID 1247888Notes

Reaction equation

HRID 1247888 reaction equation
[CH2:1]([CH2:11]/[C:12](/[CH3:25])=[CH:13]/[CH2:14][CH2:15]/[C:16](/[CH3:24])=[CH:17]/[CH2:18][CH2:19][C:20]([O:22]C)=O)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>>[CH3:26][N:27]1[CH2:32][CH2:31][N:30]([C:20](=[O:22])[CH2:19][CH2:18]/[CH:17]=[C:16](/[CH2:15][CH2:14]/[CH:13]=[C:12](\[CH3:25])/[CH2:11][CH2:1]/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])\[CH3:4])\[CH3:24])[CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 10831474HCID 10831474, compound

Product 1

HCID 644297690053-70-6Yield 51.2%

Procedure

A three-necked flask equipped with a thermometer and a stirrer was charged with 69.2 g of methyl geranylgeranylacetate and 17.0 g of N-methylpiperazine. They were heated at 150° to 200° C. in an atmosphere of nitrogen for 3 hours with stirring. After cooling, the reaction mixture was chromatographed on a column of 3 kg of silica gel using a mixture of chloroform and methanol (7:1 by volume) as an eluent, and then further chromatographed on a column of 1.5 kg of silica gel using a mixture of ethyl acetate, ethanol and benzene (1:1:1 by volume) as an eluent to give 36 g of pure N-methyl-N'-geranylgeranylacetyl piperazine [compound (2)] as an oil. The structure of the product was determined from the following analytical results.

Workup

  1. customA three-necked flask equipped with a thermometer and a stirrer
  2. temperatureThey were heated at 150° to 200° C. in an atmosphere of nitrogen for 3 hours
  3. temperatureAfter cooling
  4. customthe reaction mixture was chromatographed on a column of 3 kg of silica gel using
  5. additiona mixture of chloroform and methanol (7:1 by volume) as an eluent
  6. customfurther chromatographed on a column of 1.5 kg of silica gel using
  7. additiona mixture of ethyl acetate, ethanol and benzene (1:1:1 by volume) as an eluent

Sources & evidence

ORD record
ord-b493fe4c672c4fd3815003af98ec550b
Source dataset
uspto-grants-1985_06
Patent number
US04521417

Reaction notes

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