Ethylamine → N-Ethyl-1-isopropylcyclohexanecarboxamide

HRID 848439Notes

Reaction equation

HRID 848439 reaction equation
[CH:1]([C:4]1([C:10]([OH:12])=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)([CH3:3])[CH3:2].S(Cl)([Cl:15])=O.[CH2:17]([NH2:19])[CH3:18]>CCOCC.O>[CH:1]([C:4]1([C:10]([Cl:15])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH2:17]([NH:19][C:10]([C:4]1([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1)=[O:11])[CH3:18]

Participants

7

Reactant 3

HCID 6341EthylamineHCID 24386Thionyl ChlorideHCID 22564104HCID 22564104, compound

Product 2

HCID 3016622N-Ethyl-1-isopropylcyclohexanecarboxamideHCID 12769379HCID 12769379, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

1-isopropylcyclohexanoyl chloride was prepared from 1-isopropylcyclohexanoic acid and thionyl chloride. A solution of this acid chloride (2.6 g) in ether (25 ml) was added dropwise to a stirred solution of ethylamine (5 ml of a 70% solution in water) in ether (100 ml). After 2 hours the ethereal solution was washed with dilute hydrochloric acid and water, dried (MgSO4) and concentrated to give a white solid. This was recrystallised from petroleum ether (bp. 40°-60°) to give N-ethyl-1-isopropylcyclohexanamide, mp. 101°-2°.

Workup

  1. washAfter 2 hours the ethereal solution was washed with dilute hydrochloric acid and water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto give a white solid
  5. customThis was recrystallised from petroleum ether (bp. 40°-60°)

Sources & evidence

ORD record
ord-22692b083820459eba1054146fe63cfa
Source dataset
uspto-grants-1981_10
Patent number
US04296093

Reaction notes

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