Pyridine → Mapenterol hydrochloride

HRID 1111935Notes

Reaction equation

Br.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([OH:17])[CH2:10][NH:11][C:12]([CH2:15][CH3:16])([CH3:14])[CH3:13])=[CH:5][C:4]=1[C:18]([F:21])([F:20])[F:19].N1C=CC=CC=1.[Cl-:28].[Cl-].IC1C=CC=CC=1>O1CCCC1>[ClH:28].[NH2:2][C:3]1[C:4]([C:18]([F:19])([F:20])[F:21])=[CH:5][C:6]([CH:9]([OH:17])[CH2:10][NH:11][C:12]([CH2:15][CH3:16])([CH3:13])[CH3:14])=[CH:7][C:8]=1[Cl:28]

Participants

Conditions

Temperature: 0 °C

Procedure

0.37 gm of 1-(4'-amino-3'-trifluoromethyl-phenyl)-2-tert.pentylamino-ethanol hydrobromide and 0.2 ml of pyridine were dissolved in 30 ml of tetrahydrofuran, and the solution was cooled to 0° C. 0.3 gm of iodobenzene dichloride was added, the mixture was held for 2 hours at 0° C., and 0.1 gm of iodobenzene dichloride was again added. After standing for 20 hours at about 4° C., the solution was evaporated, distributed between ethyl acetate and water, the aqueous phase was made alkaline with 2N ammonia, and the solution was again extracted with ethyl acetate. The organic phase was washed with water, dried and a few drops of isopropanolic 4N hydrochloric acid were added. The precipitated hydrochloride of the above-mentioned compound was suction-filtered off and washed with ether. M.p. 176°-178° C. (decomp.).

Workup

waitAfter standing for 20 hours at about 4° C.
customthe solution was evaporated
extractionthe solution was again extracted with ethyl acetate
washThe organic phase was washed with water
customdried
additiona few drops of isopropanolic 4N hydrochloric acid were added
filtrationThe precipitated hydrochloride of the above-mentioned compound was suction-filtered off
washwashed with ether

Sources & evidence

ORD record: ord-626dc17b0aa648db9389c1cb0ec9129c
Source dataset: uspto-grants-1978_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04119710

Reaction notes

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