2-Aminotetralin → 1-[7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-(1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane

HRID 1380890Notes

Reaction equation

HRID 1380890 reaction equation
[CH3:1][O:2][C:3]1[C:18]([O:19][CH3:20])=[CH:17][C:6]2[CH2:7][C:8](=[O:16])[N:9]([CH2:12][CH2:13][CH:14]=O)[CH:10]=[CH:11][C:5]=2[CH:4]=1.[NH2:21][CH:22]1[CH2:31][CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23]1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[C:18]([O:19][CH3:20])=[CH:17][C:6]2[CH2:7][C:8](=[O:16])[N:9]([CH2:12][CH2:13][CH2:14][NH:21][CH:22]3[CH2:31][CH2:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:23]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 346772-AminotetralinHCID 135796613-(7,8-dimethoxy-2-oxo-1,2-dihydro-3H-benzo[d]azepin-3-yl)propanal

Product 1

HCID 135796621-[7,8-Dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-(1,2,3,4-tetrahydronaphth-2-yl)-amino]-propane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Here, 3-[7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl]-propionaldehyde (1.5 g, 0.0054 mol) and 2-amino-1,2,3,4-tetrahydronaphthalene (0.8 g, 0.0054 mol) are hydrogenated in ethanol (150 ml) in the presence of 10% palladium/charcoal (0.5 g) for 15 hours under pressure (5 bar) at 60° C. The catalyst is removed by suction filtering, the filtrate is concentrated in vacuo and the residue is purified over silica gel by column chromatography with methylene chloride and increasing amounts of ethanol (up to 4%). The clean fractions are concentrated by evaporation and the hydrochloride is precipitated from acetone. Yield: 1.35 g. Mp: 229°-230° C.

Workup

  1. customThe catalyst is removed by suction
  2. filtrationfiltering
  3. concentrationthe filtrate is concentrated in vacuo
  4. customthe residue is purified over silica gel by column chromatography with methylene chloride
  5. temperatureincreasing amounts of ethanol (up to 4%)
  6. concentrationThe clean fractions are concentrated by evaporation
  7. customthe hydrochloride is precipitated from acetone

Sources & evidence

ORD record
ord-eaea6d176e1c47688b1d0ac649616a50
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

Loading…