Dimethylamine, hydrochloride → HCID 11810425, compound

HRID 635378Notes

Reaction equation

HRID 635378 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

HCID 11810425HCID 11810425, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-08e64e07c208432b9a13429078ac7a26
Source dataset
uspto-grants-2001_02
Patent number
US06187805B1

Reaction notes

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