Dimethylamine, hydrochloride → HCID 11810425、化合物

HRID 635378ノート

反応式

HRID 635378 の反応式
C[Al](C)C.Cl.[CH3:6][NH:7][CH3:8].C([O:11][C:12](=O)[CH2:13][CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH:17]=[CH:18][N:19]2[S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25])C>C1C=CC=CC=1>[CH3:6][N:7]([CH3:8])[C:12](=[O:11])[CH2:13][CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH:17]=[CH:18][N:19]2[S:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])=[O:25]

参加物

5

反応物 3

HCID 10473Dimethylamine, hydrochlorideHCID 11057421HCID 11057421、化合物HCID 16682925Trimethylaluminum

生成物 1

HCID 11810425HCID 11810425、化合物

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

実験手順

Trimethylaluminium (1.4 ml, 2M solution in hexanes) was added to a suspension of dimethylamine hydrochloride (228 mg, 2.8 mmol) in 10 ml benzene. The reaction was allowed to stir for 1 h before dropwise addition of a solution of 3-[1-(benzenesulphonyl)-1H-indol-4-yl]propionic acid ethyl ester (0.5 g, 1.4 mmol) in benzene (10 ml). The reaction was heated at reflux for 18 h, allowed to cool and then quenched by addition of HCl (2N, 5 ml). The reaction was partitioned between H2O-EtOAc. The organic phase was washed with brine, dried (MgSO4), and concentrated to give the title compound as an oil which crystallised (527 mg, 100%); δH (CDCl3, 250 MHz), 2.63 (2H, t, J=7.5 Hz), 2.79 (2H, br s), 3.16 (2H, t, J=8.5 Hz), 6.74 (1H, d, J=0.7 Hz), 6.08 (1H, d, J=7.5 Hz), 7.21-7.27 (1H, m), 7.41-7.58 (4H, m), 7.84-7.90 (3H, m).

後処理

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 18 h
  3. temperatureto cool
  4. customquenched by addition of HCl (2N, 5 ml)
  5. customThe reaction was partitioned between H2O-EtOAc
  6. washThe organic phase was washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-08e64e07c208432b9a13429078ac7a26
出典データセット
uspto-grants-2001_02
特許番号
US06187805B1

反応ノート

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