Hydrochloric Acid → HCID 24955780, compound

HRID 1095563Notes

Reaction equation

HRID 1095563 reaction equation
[CH2:1]([C:5]1([N:23]([CH3:25])[CH3:24])[CH2:10][CH2:9][CH:8]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH:20]2[CH2:22][CH2:21]2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[ClH:26]>ClC(Cl)Cl.CO.CC(O)C>[ClH:26].[CH2:1]([C:5]1([N:23]([CH3:25])[CH3:24])[CH2:6][CH2:7][CH:8]([C:11]2[NH:12][C:13]3[C:18]([C:19]=2[CH:20]2[CH2:21][CH2:22]2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9][CH2:10]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 24955781HCID 24955781, compound

Product 1

HCID 24955780HCID 24955780, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

1-Butyl-4-(3-cyclopropyl-1H-indol-2-yl)-N,N-dimethylcyclohexanamine (polar diastereomer) (135 mg, 0.398 mmol) was dissolved in trichloromethane (15 ml) and methanol (10 ml), and a 5 N hydrochloric acid (0.16 ml. 0.8 mmol) in propan-2-ol was added. The lilac-coloured solution was concentrated and diethyl ether (40 ml) was added. After 30 min the hydrochloride was separated off as a lilac-coloured solid by filtration and washing with diethyl ether (2×2 ml). Example 135 was obtained in a yield of 56% (84 mg) with a melting point of 274-276° C.

Workup

  1. concentrationThe lilac-coloured solution was concentrated
  2. additiondiethyl ether (40 ml) was added
  3. customAfter 30 min the hydrochloride was separated off as a lilac-coloured solid by filtration
  4. washwashing with diethyl ether (2×2 ml)
  5. customExample 135 was obtained in a yield of 56% (84 mg) with a melting point of 274-276° C.

Sources & evidence

ORD record
ord-51525490b2794d6581f5874a12285452
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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