n-Butyl carbamate → Butyl N-[3-[[(butoxycarbonyl)amino]methyl]-3,5,5-trimethylcyclohexyl]carbamate

HRID 2166659Notes

Reaction equation

HRID 2166659 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:7][C:6]([CH2:9][NH2:10])([CH3:8])[CH2:5][CH:4]([NH2:11])[CH2:3]1.[C:13](=[O:20])([O:15][CH2:16][CH2:17][CH2:18][CH3:19])N>C(O)CCC>[CH2:16]([O:15][C:13]([NH:11][CH:4]1[CH2:5][C:6]([CH3:8])([CH2:9][NH:10][C:13]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:20])[CH2:7][C:2]([CH3:12])([CH3:1])[CH2:3]1)=[O:20])[CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 11596n-Butyl carbamateHCID 17857Isophorone diamine

Product 1

HCID 11100732Butyl N-[3-[[(butoxycarbonyl)amino]methyl]-3,5,5-trimethylcyclohexyl]carbamate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

766 g of isophorone diamine (3-aminomethyl-3,5,5-trimethyl-cyclohexylamine), 1054 g of n-butyl carbamate and 1000 g n-butanol were reacted in the apparatus described in Example 1 for 4.0 hours at 180° C. After the apparatus had cooled and the pressure had been reduced, the reaction mixture was removed, filtered and analyzed by high pressure liquid chromatography. A yield of 1350 g (81% of the theoretical yield) of 1-(n-butoxy-carbonylamino)-3,3,5-trimethyl-5-(n-butoxy carbonylamino-methyl)-cyclohexane was obtained.

Workup

  1. temperatureAfter the apparatus had cooled
  2. customthe reaction mixture was removed
  3. filtrationfiltered

Sources & evidence

ORD record
ord-bd9c626caae54171a32eb2b8816a8dbf
Source dataset
uspto-grants-1983_06
Patent number
US04388238

Reaction notes

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