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

HRID 76024ノート

反応式

HRID 76024 の反応式
[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

参加物

5

反応物 2

HCID 67020338(1R)-2-((2-(4-Nitrophenyl)ethyl)amino)-1-phenylethan-1-ol--hydrogen chloride (1/1)HCID 178418361HCID 178418361、化合物2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 887Methanol溶媒

反応条件

温度
20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5772c3c22d2c4f81afd86e9fe57458cf
出典データセット
uspto-grants-2014_09
特許番号
US08835474B2

反応ノート

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