Triethylamine → 5-Oxo-5-(4-phenylpiperazin-1-yl)pentanal

HRID 1942406노트

반응식

HRID 1942406 반응식
C(Cl)(=O)C(Cl)=O.[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)=[O:13].C(N(CC)CC)C>ClCCl.CS(C)=O.[Cl-].[Na+].O>[O:13]=[C:12]([N:14]1[CH2:15][CH2:16][N:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:18][CH2:19]1)[CH2:11][CH2:10][CH2:9][CH:8]=[O:7]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 669376015-Hydroxy-1-(4-phenylpiperazin-1-yl)pentan-1-one

생성물 1

HCID 866513155-Oxo-5-(4-phenylpiperazin-1-yl)pentanal

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매2회HCID 6344Dichloromethane용매3회HCID 57417360Sodium chloride; water용매

실험 절차

A solution of 1.11 mL (12.8 mmol) oxalyl chloride in 35 mL of dichloromethane is cooled to −80° C. under argon atmosphere. 2.33 mL (32.7 mmol) of dimethylsulfoxide in 9.33 mL of dichloromethane is introduced dropwise over 10 minutes. After 5 minutes a solution of 1.84 (7 mmol) 5-hydroxy-1-(4-phenylpiperazin-1-yl)pentan-1-one in 8 mL dichloromethane and 2 mL dimethylsulfoxide is added over the course of 10 minutes. The reaction mixture is stirred for another hour at −80° C. before 5 mL of triethylamine is added and the mixture is allowed to warm up to room temperature. 50 mL of saturated brine solution is added for hydrolysis. The organic phase is separated, extracted three times with a saturated solution of sodium chloride, dried over sodium sulfate and the solvent is evaporated. The crude product is obtained in almost quantitative yield.

후처리

  1. additionis added
  2. customThe organic phase is separated
  3. extractionextracted three times with a saturated solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated

출처 및 근거

ORD 기록
ord-d48f935d23634ba298dd4290c79c7b38
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389555B2

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