Isopropylamine → HCID 20531641, compound

HRID 1759313Notes

Reaction equation

HRID 1759313 reaction equation
[O:1]1[CH2:17][CH:2]1[CH2:3][O:4][C:5]1[C:10]2[CH2:11][CH2:12][CH2:13][C:14](=[O:16])[NH:15][C:9]=2[CH:8]=[CH:7][CH:6]=1.[CH:18]([NH2:21])([CH3:20])[CH3:19]>C(O)CC>[OH:1][CH:2]([CH2:17][NH:21][CH:18]([CH3:20])[CH3:19])[CH2:3][O:4][C:5]1[C:10]2[CH2:11][CH2:12][CH2:13][C:14](=[O:16])[NH:15][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 232893091,3,4,5-Tetrahydro-6-(2-oxiranylmethoxy)-2H-1-benzazepin-2-one

Product 1

HCID 20531641HCID 20531641, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

3.3 g (0.014 mole) of 6-(2,3-epoxypropoxy)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one are dissolved in 400 ml of n-propanol, 3 g of isopropylamine are added and the mixture is kept on a boiling waterbath for from 4 to 6 hours. The solvent and excess amine are then distilled off on a rotary evaporator and the residue is twice taken up in methanol, the solvent again being distilled off. The residue thus obtained is chromatographed on a silica gel column, using methanol as the mobile phase. 1.65 g (39.9% yield) of 6-(2-hydroxy-3-isopropylaminopropoxy)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one, of melting point 143°-145° C., are obtained.

Workup

  1. customis kept on a boiling waterbath for from 4 to 6 hours
  2. distillationThe solvent and excess amine are then distilled off on a rotary evaporator
  3. distillationthe solvent again being distilled off
  4. customThe residue thus obtained
  5. customis chromatographed on a silica gel column

Sources & evidence

ORD record
ord-f18c00fd1fcd495e90de05f28b5dc881
Source dataset
uspto-grants-1982_07
Patent number
US04340595

Reaction notes

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