Ethyl 4-aminocyclohexanecarboxylate → Ethyl 4-(4-acetoxy-3-methoxycinnamamido)-1-cyclohexanecarboxylate

HRID 2225510Notes

Reaction equation

HRID 2225510 reaction equation
[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11](Cl)=[O:12])=[CH:7][C:6]=1[O:16][CH3:17])(=[O:3])[CH3:2].[NH2:18][CH:19]1[CH2:24][CH2:23][CH:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:20]1>N1C=CC=CC=1>[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11]([NH:18][CH:19]2[CH2:20][CH2:21][CH:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:23][CH2:24]2)=[O:12])=[CH:7][C:6]=1[O:16][CH3:17])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 409963Ethyl 4-aminocyclohexanecarboxylateHCID 544680224-Acetoxy-3-methoxycinnamoyl chloride

Product 1

HCID 53918885Ethyl 4-(4-acetoxy-3-methoxycinnamamido)-1-cyclohexanecarboxylateYield 60.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Using 2.5 g of 4-acetoxy-3-methoxycinnamoyl chloride, 3.7 g of ethyl 4-amino-1-cyclohexanecarboxylate described in the literature [V. Skaric, M. Kovacevic, and D. Skaric, J. Chem. Soc. Perkin I, 1199-1201 (1976)], and 100 ml of pyridine, a reaction similar to that conducted in Example 53 was carried out. As a result, 2.3 g of ethyl 4-(4-acetoxy-3-methoxycinnamamido)-1-cyclohexanecarboxylate (a compound of the present invention) was obtained as pale yellowish white crystal, which had the following physiochemical properties:

Workup

  1. customa reaction similar to

Sources & evidence

ORD record
ord-6ac29d7785e14453afe36451965d392d
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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