(1R)-2-((2-(4-Nitrophenyl)ethyl)amino)-1-phenylethan-1-ol--hydrogen chloride (1/1) → 2-((4-Aminophenethyl)amino)-1-phenylethanol hydrochloride, (R)-

HRID 2353383Notes

Reaction equation

[ClH:1].[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][CH2:14][C@@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[OH:16])=[CH:7][CH:6]=1)([O-])=O.[H][H]>[C].[Pd].CO>[ClH:1].[NH2:2][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][NH:13][CH2:14][C@@H:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[OH:16])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 11.0 kg of (R)-2-[[2-(4-nitrophenyl)ethyl]amino]-1-phenylethanol monohydrochloride, 110 liters of methanol and 1.20 kg of wet 10% palladium-carbon (wetting rate: 54.2%) was stirred in a hydrogen atmosphere until absorption of hydrogen stopped. The reaction solution was filtered and the filtrate was concentrated in vacuo. Methanol (40 liters) was added to the residue to dissolve at 40° C. and crystallization was conducted by addition of 220 liters of diisopropyl ether thereto followed by stirring at 20° C. throughout one night. The crystals were filtered and washed with 30 liters of diisopropyl ether. They were dried in vacuo to give 9.43 kg of (R)-2-[[2-(4-aminophenyl)ethyl]amino]-1-phenylethanol monohydrochloride.

Workup

filtrationThe reaction solution was filtered
concentrationthe filtrate was concentrated in vacuo
additionMethanol (40 liters) was added to the residue
dissolutionto dissolve at 40° C.
customcrystallization
additionwas conducted by addition of 220 liters of diisopropyl ether
filtrationThe crystals were filtered
washwashed with 30 liters of diisopropyl ether
customThey were dried in vacuo

Sources & evidence

ORD record: ord-faf2ffd1325444ca823d7eeaedb41f68
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750029B2

Reaction notes

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