N,N-Dimethylcyclohexylamine → HCID 10955654, compound

HRID 1740690Notes

Reaction equation

[C:1]1(=[O:8])[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C1CCCCC1)C.[C:18](Cl)(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C1(C)C=CC=CC=1>[C:18]([N:7]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]1=[O:8])(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

Conditions

Temperature: 67.5 °C

Procedure

113 g (1 mol) of ε-caprolactam (purity >99% by weight) are dissolved in 200 ml of toluene in a round-bottom flask. 127 g (1 mol) of N,N-dimethylcyclohexylamine are introduced into this. Then, at 40-70° C., 164.2 g (1 mol) of octanoyl chloride (purity 99% by weight) are added dropwise. The reaction mixture is then stirred at 65-70° C. for one hour. Then, to remove the ammonium salt produced, it is washed first once with 130 ml of hot water and then with 10 ml of concentrated HCl dissolved in 130 ml of hot water. It is subsequently washed 3 more times with 130 ml of hot water in order to maintain a pH of 5-7 in the reaction mixture. The solvent is distilled off under reduced pressure (water pump) at 70-80° C. N-octanoylcaprolactam is obtained as a yellow liquid in 93% yield with a purity of 98%.

Workup

customThen, to remove the ammonium salt
customproduced
washit is washed first once with 130 ml of hot water
dissolutionwith 10 ml of concentrated HCl dissolved in 130 ml of hot water
washIt is subsequently washed 3 more times with 130 ml of hot water in order
temperatureto maintain a pH of 5-7 in the reaction mixture
distillationThe solvent is distilled off under reduced pressure (water pump) at 70-80° C

Sources & evidence

ORD record: ord-75ae19a0e4924ed7aa153aa7376e2a86
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05972508

Reaction notes

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