1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 53936808, compound

HRID 344553Notes

Reaction equation

HRID 344553 reaction equation
Br.Br.[NH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[O:15])[CH2:7][CH2:6]1.[NH2:23][C:24]1[C:32]([Cl:33])=[CH:31][C:27]([C:28](O)=[O:29])=[C:26]([O:34][CH3:35])[CH:25]=1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>C(N(CC)CC)C>[NH2:23][C:24]1[C:32]([Cl:33])=[CH:31][C:27]([C:28]([NH:3][CH2:4][CH:5]2[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][C:14]([C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=3)=[O:15])[CH2:7][CH2:6]2)=[O:29])=[C:26]([O:34][CH3:35])[CH:25]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 70074581HCID 70074581, compound

Product 1

HCID 53936808HCID 53936808, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

4-Aminomethyl-1-(4-(4-hydroxyphenyl)-4-oxobutyl)piperidine dihydrobromide (3.67 g) as a starting compound, 4-amino-5-chloro-2-methoxybenzoic acid (1.69 g), triethylamine (4.65 ml), 1-hydroxybenzotriazole (1.20 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.69 g) were reacted and purified in the same manner as in Example 270 to give 3.03 g of 4-amino-5-chloro-2-methoxy-N-((1-(4-(4-hydroxyphenyl)-4-oxobutyl)piperidin-4-yl)methyl)benzamide, m.p. 199°-201° C.

Workup

  1. custompurified in the same manner as in Example 270

Sources & evidence

ORD record
ord-adae4b15ad754f3b8652d301f62f9f3f
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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