2,3-dihydro-1H-indol-1-amine → HCID 22021744, compound

HRID 1292865Notes

Reaction equation

HRID 1292865 reaction equation
N[N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.O.[ClH:12].[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=O>C(O)(C)C>[ClH:12].[CH:8]1[CH:7]=[CH:6][C:5]2[CH2:4][CH2:3][N:2]3[C:10]=2[C:9]=1[C:17]1[CH2:18][NH:13][CH2:14][CH2:15][C:16]=13

Participants

4

Reactant 2

HCID 27609322,3-dihydro-1H-indol-1-amineHCID 22021827Piperidone monohydrate hydrochloride

Product 1

HCID 22021744HCID 22021744, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 1-amino-2,3-dihydroindole (1.0 g, 5.9 mmol), piperidone hydrochloride monohydrate (0.91 g, 5.9 mmol) and isopropanol (29 mL) was brought to reflux for 4 hours. The resulting brown solid was filtered and washed with cold diethylether (20 mL) and dried under vacuum, affording the title compound (1.01 g, 74%). 1H NMR (CD3OD, 300 MHz) δ 7.15 (d, 1H, J=7.7 Hz), 6.85-6.96 (m, 2H), 4.39-4.50 (m, 4H), 3.75 (t, 2H, J=7.3 Hz), 3.57 (t, 2H, J=6.2 Hz), 3.15 (t, 2H, J=6.2 Hz) ppm.

Workup

  1. temperatureto reflux for 4 hours
  2. filtrationThe resulting brown solid was filtered
  3. washwashed with cold diethylether (20 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-06d635ae2b0143178885a2ee00c2bfe8
Source dataset
uspto-grants-2007_07
Patent number
US07238690B2

Reaction notes

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