Dimethylamine, hydrochloride → HCID 11810425, 화합물

HRID 635378노트

반응식

HRID 635378 반응식
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]

참가 물질

5

반응물 3

HCID 10473Dimethylamine, hydrochlorideHCID 11057421HCID 11057421, 화합물HCID 16682925Trimethylaluminum

생성물 1

HCID 11810425HCID 11810425, 화합물

시약·촉매·용매 1

HCID 241Benzene용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-08e64e07c208432b9a13429078ac7a26
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06187805B1

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