Ethanolamine → N-(2-hydroxyethyl)-4-[[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]methoxy]benzamide

HRID 1030913Notes

Reaction equation

[OH:1][C:2]1([CH2:15][O:16][C:17]2[CH:26]=[CH:25][C:20]([C:21](OC)=[O:22])=[CH:19][CH:18]=2)[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[NH2:27][CH2:28][CH2:29][OH:30]>O>[OH:30][CH2:29][CH2:28][NH:27][C:21](=[O:22])[C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:15][C:2]2([OH:1])[CH2:3][CH2:4][N:5]([CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:6][CH2:7]2)=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 145 °C

Procedure

A mixture of 10.7 parts of methyl 4-[[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]methoxy]benzoate and 8 parts of 2-aminoethanol was stirred for 4 hours in an oil bath at 145° C. After cooling, the reaction mixture was poured into water. The oil was decanted, washed twice with water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from a mixture of 2,2'-oxybispropane and 2-propanol. The product was filtered off and dried, yielding 8 parts (69.3%) of N-(2-hydroxyethyl)-4-[[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]methoxy]benzamide; mp. 161.1° C. (int. 80).

Workup

temperatureAfter cooling
customThe oil was decanted
washwashed twice with water
extractionthe product was extracted with dichloromethane
customThe extract was dried
filtrationfiltered
customevaporated
customThe residue was crystallized from a mixture of 2,2'-oxybispropane and 2-propanol
filtrationThe product was filtered off
customdried

Sources & evidence

ORD record: ord-5bb146c736ca4d9eb52ff229ac8364f4
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05106973

Reaction notes

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