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Hydrochloric Acid → 1-benzyl-N-hydroxy-4-(4-methoxyphenylsulfonyl)piperidine-4-carboxamide

HRID 2305875
ノート
印刷プレビュー

反応式

HRID 2305875 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2([C:25]([OH:27])=O)[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.Cl.C([N:37](CC)CC)C.C1COCC1.[OH2:47]>CN(C=O)C.C(Cl)Cl>[OH:47][NH:37][C:25]([C:12]1([S:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:11])=[O:10])[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)=[O:27]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 65578Oxalyl chloride2 回HCID 111436104-(4-Methoxy-benzenesulfonyl)-1-benzyl-piperidine-4-carboxylic acidHCID 21881883Oxolane--water (1/1)

生成物 1

HCID 98659361-benzyl-N-hydroxy-4-(4-methoxyphenylsulfonyl)piperidine-4-carboxamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 4-(4-Methoxy-benzenesulfonyl)-1-benzyl-piperidine-4-carboxylic acid (2.0 g, 5.1 mmol) and DMF (2 drops) in CH2Cl2 (100 ml) at OC, oxalyl chloride (1.0 gm, 8 mmol) was added in a drop-wise manner. After the addition, the reaction mixture was stirred at room temperature for 1 hour. Simultaneously, in a separate flask a mixture of hydroxylainine hydrochloride (2.0 gm, 29 mmol) and triethylamine (5 ml, excess) was stirred in THF:water (5:1, 30 ml) at 0° C. for 1 hour. At the end of 1 hour, the oxalyl chloride reaction mixture was concentrated and the pale yellow residue was dissolved in 10 ml of CH2Cl2 and added slowly to the hydroxylamine at 0° C. The reaction mixture was stirred at room temperature for 24 hours and concentrated. The residue obtained was extracted with chloroform and washed well with water. The product obtained was purified by silica gel column chromatography and eluted with chloroform the product 4-(4-Methoxy-benzenesulfonyl)-l-benzyl-piperidinefcarboxylic acid hydroxyamide was isolated as a colorless solid. mp 90-95° C.; Yield, 1.2 g, 48%; MS: 405 (M+H)+; 1H NMR (300 MHz, DMSO-d6): 8 2.29 (m, 3H), 2.76-2.79 (m, 2H), 3.43 (m, 4H),4.30 (s, 2H), 7.14-7.17 (d,2H), 7.50-7.73 (m, 5H), 9.37 (s,lH), 10.53 (s,lH), 11.18 (s,1H).

後処理

  1. additionAfter the addition
  2. concentrationwas concentrated
  3. dissolutionthe pale yellow residue was dissolved in 10 ml of CH2Cl2
  4. additionadded slowly to the hydroxylamine at 0° C
  5. stirringThe reaction mixture was stirred at room temperature for 24 hours
  6. concentrationconcentrated
  7. customThe residue obtained
  8. extractionwas extracted with chloroform
  9. washwashed well with water
  10. customThe product obtained
  11. customwas purified by silica gel column chromatography
  12. washeluted with chloroform the product 4-(4-Methoxy-benzenesulfonyl)-l-benzyl-piperidinefcarboxylic acid hydroxyamide
  13. customwas isolated as a colorless solid
  14. customYield

出典と根拠

ORDレコード
ord-99396365d597462c81522b8fb3cbf0d6
出典データセット
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06441023B1

反応ノート

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