Water → 1-Amino-1-[1-(4-chlorophenyl)cyclobutyl]-3-ethylpentan-3-ol

HRID 728278노트

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HRID 728278 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12](=[NH:20])[CH2:13][C:14]([CH2:18][CH3:19])([OH:17])[CH2:15][CH3:16])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.O.[OH-].[Na+]>O1CCCC1>[NH2:20][CH:12]([C:8]1([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:11][CH2:10][CH2:9]1)[CH2:13][C:14]([CH2:15][CH3:16])([OH:17])[CH2:18][CH3:19]

참가 물질

5

반응물 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 198237421-[1-(4-Chlorophenyl)cyclobutyl]-3-ethyl-1-iminopentan-3-ol

생성물 1

HCID 198237701-Amino-1-[1-(4-chlorophenyl)cyclobutyl]-3-ethylpentan-3-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 1-[1-(4-chlorophenyl)cyclobutyl]-3-ethyl-1-iminopentan-3-ol (1.6 g) in dry tetrahydrofuran (20 ml) was treated under nitrogen with boranetetrahydrofuran complex (1M solution in tetrahydrofuran 10 ml) and the mixture was heated under reflux for 24 hours. The mixture was cooled in ice and water and then 2N sodium hydroxide solution were added. The resulting mixture was extracted with ether and the extracts were washed, dried and evaporated to give 1-amino-1-[1-(4-chlorophenyl)cyclobutyl]-3-ethylpentan-3-ol which was then converted into the corresponding dimethylamino compound by heating a mixture of the primary amine (1.5 g), 98% formic acid (4 ml) and 37-40% aqueous formaldehyde (2 ml) at 90°-95° C. for 16 hours. The reaction mixture was cooled and poured into a mixture of 16N sodium hydroxide solution (7 ml) and ice. The mixture was extracted with ether and the extract washed, dried and evaporated to give a residue which was dissolved in ether. Addition of a solution of maleic acid in ether gave 1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylamino-3-ethylpentan-3-ol maleate (m.p. 110°-111° C.).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. temperatureThe mixture was cooled in ice
  4. extractionThe resulting mixture was extracted with ether
  5. washthe extracts were washed
  6. customdried
  7. customevaporated

출처 및 근거

ORD 기록
ord-f91dda78e00644f1ada4d4690f2d919b
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05047432

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