Isopropylamine → HCID 15437531, compound

HRID 1870257Notes

Reaction equation

HRID 1870257 reaction equation
[C:1]([CH2:4][C@@H:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:8][CH2:7][CH2:6]1)(O)=[O:2].S(Cl)(Cl)=O.CN1CCCC1=O.[CH:37]([NH2:40])([CH3:39])[CH3:38]>ClCCl>[CH:37]([NH:40][C:1]([CH2:4][C@@H:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([S:16]([C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)(=[O:17])=[O:18])[CH2:8][CH2:7][CH2:6]1)=[O:2])([CH3:39])[CH3:38]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 13387N-methyl-2-pyrrolidoneHCID 24386Thionyl ChlorideHCID 11175806HCID 11175806, compound

Product 1

HCID 15437531HCID 15437531, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (5R)-5-carboxymethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (115.6 g) in dry dichloromethane (700 ml) are added thionyl chloride (70 ml) and 1-methyl-2-pyrrolidone (1 ml), and the mixture is refluxed with stirring for three hours. The solution is added dropwise into a solution of isopropylamine (274 ml) in dichloromethane (300 ml) under ice-cooling, and the mixture is stirred for 12 hours. The mixture is evaporated under reduced pressure to remove the dichloromethane, and to the residue is added a 3N aqueous sodium hydroxide solution (1 liter), and the mixture is extracted with ethyl acetate. The organic layer is washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is recrystallized from a 75% aqueous methanol (700 ml) to give (5R)-5-isopropylaminocarbonylmethyl-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-benzazepine (63.2 g).

Workup

  1. temperaturethe mixture is refluxed
  2. temperaturecooling
  3. stirringthe mixture is stirred for 12 hours
  4. customThe mixture is evaporated under reduced pressure
  5. customto remove the dichloromethane
  6. additionto the residue is added a 3N aqueous sodium hydroxide solution (1 liter)
  7. extractionthe mixture is extracted with ethyl acetate
  8. washThe organic layer is washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue is recrystallized from a 75% aqueous methanol (700 ml)

Sources & evidence

ORD record
ord-dc1d76ee1f9b44f5818fb58c9c59ab60
Source dataset
uspto-grants-2000_08
Patent number
US06096736

Reaction notes

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