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Piperidine → Phenylmethyl alpha-[[[2-(dimethylamino)ethyl]thio]methyl]benzenepropanoate

HRID 36747
ノート
印刷プレビュー

反応式

HRID 36747 の反応式
[CH2:1]=[C:2]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].Cl.[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][SH:25].N1CCCCC1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>CO>[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][S:25][CH2:1][CH:2]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:3]([O:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8082PiperidineHCID 25798Captamine HydrochlorideHCID 66854Benzyltrimethylammonium hydroxideHCID 10912012Benzyl 2-Benzylacrylate

生成物 1

HCID 15296671Phenylmethyl alpha-[[[2-(dimethylamino)ethyl]thio]methyl]benzenepropanoate収率 24%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒
2 回

実験手順

The oil prepared in Step 10 (1.5 g, 5.95 mmol) was dissolved under argon in methanol (22 mL). To this solution was added 2-dimethylaminoethanethiol hydrochloride (843 mg, 5.95 mmol), piperidine (0.78 mL, 7.85 mmol) and benzyltrimethylammonium hydroxide (0.25 mL, 0.6 mmol), and the mixture was stirred at room temperature for 16 hours. The solvent was removed on a rotary evaporator and then the residue was purified by flash chromotography on silica gel, eluting with 20:1 CH2Cl2 :MeOH to give the pure title compound (0.5 g, 24% yield). 1H NMR: 300 MHz spectrum consistent with proposed structure. Anal: calcd. for C21H27NO2S+0.2H2O: C, 69.85; H, 7.65; N, 3.88. Found: C, 69.58; H, 7.60; N, 3.98.

後処理

  1. customThe solvent was removed on a rotary evaporator
  2. customthe residue was purified by flash chromotography on silica gel
  3. washeluting with 20:1 CH2Cl2

出典と根拠

ORDレコード
ord-41f0d75e5d4744ac88a9dca12e15411d
出典データセット
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05416119

反応ノート

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