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

HRID 2186315

反応式

HRID 2186315 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

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 887Methanol溶媒2 回

実験手順

The oil prepared in Step 9 (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 chromatography 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 chromatography on silica gel
  3. washeluting with 20:1 CH2Cl2

出典と根拠

ORDレコード
ord-38a39fce53664b6394c68d98e2f32edd
出典データセット
uspto-grants-2002_06
特許番号
US06403648B2

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