Ammonia → HCID 20287106, compound

HRID 127474Notes

Reaction equation

HRID 127474 reaction equation
[ClH:1].[OH:2][C:3]1[CH:12]=[CH:11][C:10]([CH:13]([OH:29])[CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[CH:9][C:4]=1[C:5](OC)=[O:6].Cl.OC1C=CC(C(O)[CH2:43][N:44]2CCN(C3C=CC=CC=3OC)CC2)=CC=1C(OC)=O.Cl.OC1C=CC(C(O)CN2CCN(C3C=CC=CC=3C)CC2)=CC=1C(OC)=O.CN.N>>[OH2:2].[ClH:1].[OH:2][C:3]1[CH:12]=[CH:11][C:10]([CH:13]([OH:29])[CH2:14][N:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)[CH2:19][CH2:20]2)=[CH:9][C:4]=1[C:5]([NH:44][CH3:43])=[O:6]

Participants

6

Reactant 5

HCID 222AmmoniaHCID 6329MethylamineHCID 20287095HCID 20287095, compoundHCID 20287113HCID 20287113, compoundHCID 20287125HCID 20287125, compound

Product 1

HCID 20287106HCID 20287106, compound

Procedure

Following essentially the same procedure but substituting methyl 2-hydroxy-5-[1-hydroxy-2-[4-(4-methoxyphenyl)-1-piperazinyl]ethyl]benzoate hydrochloride and methyl 2-hydroxy-5-[1-hydroxy-2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]benzoate hydrochloride for the methyl 2-hydroxy-5-[1-hydroxy-2-[4-(2-methylphenyl)-1-piperazinyl]ethyl]benzoate hydrochloride above and using gaseous methylamine in lieu of ammonia results in the preparation of 2-hydroxy-5-[1-hydroxy-2-[4-(4-methoxyphenyl)-1-piperazinyl]ethyl]-N-methylbenzamide monohydrochloride hydrate, having a m.pt. of 188°-9° C. (dec.), and 2-hydroxy-5-[1-hydroxy-2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-N-methylbenzamide monohydrochloride monohydrate, having a m.pt. of 162°-5° C. (dec.), respectively.

Sources & evidence

ORD record
ord-b0f91077220e4616b059853b58ca3804
Source dataset
uspto-grants-1981_03
Patent number
US04255575

Reaction notes

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