Hydrochloric Acid → HCID 21952620, compound

HRID 735204Notes

Reaction equation

HRID 735204 reaction equation
[ClH:1].[I:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9]N.Cl.O.[NH:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.Cl>C(O)C(F)(F)F>[ClH:1].[I:2][C:3]1[C:4]2[NH:9][C:16]3[CH2:17][CH2:18][NH:13][CH2:14][C:15]=3[C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723901PiperonylamineHCID 12326100HCID 12326100, compound

Product 1

HCID 21952620HCID 21952620, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Procedure

1-(2-iodophenyl)hydrazine hydrochloride (1.67 g, 6.2 mmol) and 4-piperidone monohydrate hydrochloride (0.952 g, 6.2 mmol) were dissolved in trifluoroethanol (15 mL) and concentrated hydrochloric acid (5 mL) and heated at 87° C. and stirred for 3 h. The solid was filtered, washed with cold isopropyl alcohol (50 mL), and dried to give 6-iodo-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride (1.76 g, 85%) as a tan solid. 1H NMR (CD3OD, 300 MHz) δ 7.49 (d, 1H, J=7.7 Hz), 7.43 (d, 1H, J=8 Hz), 6.82 (t, 1H, J=7.7 Hz), 4.40 (s, 2H), 3.60 (t, 2H, J=6.25 Hz), 3.18 (t, 2H, J=5.85 Hz) ppm.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with cold isopropyl alcohol (50 mL)
  3. customdried

Sources & evidence

ORD record
ord-fd595a76d00d46daa9ea65eb59ae8f98
Source dataset
uspto-grants-2009_09
Patent number
US07592454B2

Reaction notes

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