(R)-1-Phenylpropylamine → HCID 70023804, compound

HRID 1358286Notes

Reaction equation

HRID 1358286 reaction equation
Cl.[Cl:2][C:3]1[C:4]2[NH:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:5]=2[N:6]=[CH:7][N:8]=1.C[CH2:17][C@@H:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[ClH:2].[C:19]1([C@H:18]([NH:25][C:3]2[C:4]3[NH:15][C:14]4[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=4[C:5]=3[N:6]=[CH:7][N:8]=2)[CH3:17])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 5324978(R)-1-PhenylpropylamineHCID 181843684-Chloro-5H-pyrimido[5,4-b]indole--hydrogen chloride (1/1)

Product 1

HCID 70023804HCID 70023804, compoundYield 11%

Procedure

4-Chloroindolo[3,2-d]pyrimidine hydrochloride 240 mg, 1 mmol) and (R)-(+)-methylbenzylamine (1 ml) are stirred under a dry nitrogen atmosphere at 150 for 5 hours, and then concentrated under reduced pressure to an oil. This oil is dissolved in EtOAc (20 ml), and stirred for 16 h. The precipitate which forms is collected by filtration, washed with EtOAc, and dried at 90 in vacuo to give 4-([R]-1-phenylethylamino)indolo[3,2-d]pyrimidine hydrochloride (37 mg, 11%). 1H NMR (DMSO): δ10 (1H, s), 9.14 (1H, brs), 8.64 (1H, s), 8.16 (1H, d, J=8.0 Hz), 7.74 (1H, d, J=8.5 Hz), 7.63-7.59 (1H, m), 7.50 (2H, d, J=7.2 Hz), 7.38-7.24 (4H, m), 5.59 (1H, p, J=7.0 Hz); 1.64 (3H, d, J=7.0 Hz).

Workup

  1. concentrationconcentrated under reduced pressure to an oil
  2. dissolutionThis oil is dissolved in EtOAc (20 ml)
  3. filtrationThe precipitate which forms is collected by filtration
  4. washwashed with EtOAc
  5. customdried at 90 in vacuo

Sources & evidence

ORD record
ord-e90345f13f0946a8bb8a07ad862bfb6f
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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