Ethyl 3-(4-aminophenyl)propanoate → Ethyl 4-[15-(trifluoromethyl)pentadecylamino]hydrocinnamate

HRID 1105923Notes

Reaction equation

HRID 1105923 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.[F:15][C:16]([F:34])([F:33])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]Br>>[F:15][C:16]([F:33])([F:34])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 10442595Ethyl 3-(4-aminophenyl)propanoateHCID 1279729815-(Trifluoromethyl)pentadecyl bromide

Product 1

HCID 20549401Ethyl 4-[15-(trifluoromethyl)pentadecylamino]hydrocinnamate

Procedure

In a manner directly analogous to that described in Example 8, ethyl 4-aminohydrocinnamate is alkylated with 15-(trifluoromethyl)pentadecyl bromide to form ethyl 4-[15-(trifluoromethyl)pentadecylamino]hydrocinnamate. Subsequently, in a manner directly analogous to that described in Example 9, ethyl 4-[15-(trifluoromethyl)pentadecylamino]hydrocinnamate is hydrolyzed to 4-[15-(trifluoromethyl)pentadecylamino]hydrocinnamic acid.

Sources & evidence

ORD record
ord-caeb0d65111a476c91cb2e4752760169
Source dataset
uspto-grants-1982_01
Patent number
US04310545

Reaction notes

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