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

HRID 76024노트

반응식

HRID 76024 반응식
[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

참가 물질

5

반응물 2

HCID 67020338(1R)-2-((2-(4-Nitrophenyl)ethyl)amino)-1-phenylethan-1-ol--hydrogen chloride (1/1)HCID 178418361HCID 178418361, 화합물2회

생성물 1

HCID 529530072-((4-Aminophenethyl)amino)-1-phenylethanol hydrochloride, (R)-수율 94.5%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 887Methanol용매

반응 조건

온도
20 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-5772c3c22d2c4f81afd86e9fe57458cf
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835474B2

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