Hydrochloric Acid → HCID 21952766, compound

HRID 2215898Notes

Reaction equation

HRID 2215898 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9]N.O.[NH:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.[ClH:21]>C(O)(C)C>[ClH:21].[ClH:21].[F:1][C:2]([F:12])([F:11])[C:3]1[C:4]2[NH:9][C:17]3[CH2:18][CH2:19][NH:14][CH2:15][C:16]=3[C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5208002-(Trifluoromethyl)phenylhydrazineHCID 21584170Piperidin-4-one hydrate

Product 1

HCID 21952766HCID 21952766, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of (2-trifluoromethyl-phenyl)-hydrazine (12.0 g, 68.13 mmol) and 4-piperidone monohydrate (10.46 g, 68.09 mmol), in iso-propyl alcohol was bubbled HCl (g) for 15 minutes at rt. The reaction was sealed in a pressure vessel and heated to 95° C. for 5 h, then cooled to rt. The reaction mixture was filtered and washed with iso-propyl alcohol and dried in vacuo to yield 6-trifluoromethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole bis-hydrochloride as a white solid (13.3 g, 63% yield). 1H NMR (CD3OD, 300 MHz) δ 3.203 (t, 2H, 12.4 Hz), 3.642 (t, 2H, 12.0 Hz), 4.472 (t, 2H, 2.6 Hz), 7.189 (t, 1H, 15.7 Hz), 7.435 (d, 1H, 7.7 Hz), 7.709 (d, 1H, 8.0 Hz) ppm.

Workup

  1. customThe reaction was sealed in a pressure vessel
  2. temperaturecooled to rt
  3. filtrationThe reaction mixture was filtered
  4. washwashed with iso-propyl alcohol
  5. customdried in vacuo

Sources & evidence

ORD record
ord-d0899ca6267240069ddc1a624840cdc0
Source dataset
uspto-grants-2006_09
Patent number
US07109339B2

Reaction notes

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