Dichloromethane → 1-(Methoxycarbonyl)propyl 4-(cyclohex-3-enylmethylamino)hydrocinnamate

HRID 2166781Notes

Reaction equation

HRID 2166781 reaction equation
Cl.[CH:2]1([CH2:8][NH:9][C:10]2[CH:20]=[CH:19][C:13]([CH2:14][CH2:15][C:16](Cl)=[O:17])=[CH:12][CH:11]=2)[CH2:7][CH2:6][CH:5]=[CH:4][CH2:3]1.C(Cl)Cl.[OH:24][CH:25]([CH2:30][CH3:31])[C:26]([O:28][CH3:29])=[O:27].C(N(CC)CC)C>CCOCC>[CH:2]1([CH2:8][NH:9][C:10]2[CH:20]=[CH:19][C:13]([CH2:14][CH2:15][C:16]([O:24][CH:25]([C:26]([O:28][CH3:29])=[O:27])[CH2:30][CH3:31])=[O:17])=[CH:12][CH:11]=2)[CH2:7][CH2:6][CH:5]=[CH:4][CH2:3]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 520445Methyl 2-hydroxybutanoateHCID 204989384-(Cyclohex-3-enylmethylamino)hydrocinnamoyl chloride hydrochloride

Product 1

HCID 204990261-(Methoxycarbonyl)propyl 4-(cyclohex-3-enylmethylamino)hydrocinnamate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 10.0 g. 4-(cyclohex-3-enylmethylamino)hydrocinnamoyl chloride hydrochloride in 200 ml. methylene chloride is added dropwise a solution of 3 g. methyl 2-hydroxybutyrate and 5 g. triethylamine in 100 ml. ether. After 17 hours stirring at room temperature, the precipitate is collected and washed with several portions of ether. The ether solution is washed with water, dried and evaporated to yield 1-(methoxycarbonyl)propyl 4-(cyclohex-3-enylmethylamino)hydrocinnamate as a white solid.

Workup

  1. customthe precipitate is collected
  2. washwashed with several portions of ether
  3. washThe ether solution is washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-e4e4026e217249e888d8090e2ab02cf7
Source dataset
uspto-grants-1983_06
Patent number
US04388459

Reaction notes

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