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

HRID 1942406ノート

反応式

HRID 1942406 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 6344Dichloromethane溶媒3 回HCID 57417360Sodium chloride; water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d48f935d23634ba298dd4290c79c7b38
出典データセット
uspto-grants-2013_03
特許番号
US08389555B2

反応ノート

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