Water → (S)-1,4-dibenzyl-2-vinylpiperazine

HRID 131391ノート

反応式

HRID 131391 の反応式
C(O)(=O)C(C1C=CC=CC=1)O.[CH2:12]([N:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:21][C@@H:20]1[CH:32]=[CH2:33])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.[OH-].[Na+]>CC(OC)(C)C>[CH2:12]([N:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:21][C@@H:20]1[CH:32]=[CH2:33])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 69215334(s)-1,4-Dibenzyl-2-vinyl-piperazine mandelic acid salt

生成物 1

HCID 17759473(S)-1,4-dibenzyl-2-vinylpiperazine収率 99.7%

試薬・触媒・溶媒 1

HCID 15413tert-Butyl methyl ether溶媒

実験手順

Combine (S)-1,4-dibenzyl-2-vinyl-piperazine mandelic acid salt (200.0 g, 0.450 mol), water (1 L), and 5N sodium hydroxide (112.5 mL, 0.562 mol) and stir at ambient temperature for 15 minutes. Add MTBE (1 L) and stir at ambient temperature for 1 hour. Layer separate and wash the organics with water (2×1 L). Dry the organics over sodium sulfate, filter and concentrate in vacuo to afford 131.2 g of the title compound as an oil (99.7%). 1H NMR (500 MHz, DMSO-d6) δ 2.00 (bt, 1H), 2.07 (d, 2H), 2.56 (m, 1H), 2.58 (d, 2H), 2.84 (t, 1H), 3.02 (d, 1H), 3.49 (s, 2H), 3.91 (d, 1H), 5.15 (d, 1H), 5.25 (d, 1H), 5.81 (m, 1H), 7.27 (m, 10H). MS (ES+) M+H calcd for C20H24N2 292.43; found 293.10.

後処理

  1. customLayer separate
  2. washwash the organics with water (2×1 L)
  3. dry with materialDry the organics over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

出典と根拠

ORDレコード
ord-2c24091a62b3424e8e1cf2377cd188d0
出典データセット
uspto-grants-2008_06
特許番号
US07384934B2

反応ノート

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