Hydrochloric Acid → 9-[2-(1-Piperidinyl)ethyl]-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole monohydrochloride

HRID 482321Notes

Reaction equation

HRID 482321 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]3[C:18]([N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)=[N:19][C:20]([N:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)=[N:21][C:10]2=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:32]>C(O)C>[ClH:32].[N:1]1([CH2:7][CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]3[C:18]([N:27]4[CH2:28][CH2:29][CH2:30][CH2:31]4)=[N:19][C:20]([N:22]4[CH2:23][CH2:24][CH2:25][CH2:26]4)=[N:21][C:10]2=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 190640859-[2-(1-Piperidinyl)ethyl]-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole

Product 1

HCID 867530329-[2-(1-Piperidinyl)ethyl]-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole monohydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 9-[2-(1-piperidinyl)ethyl]-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole (I, EXAMPLE5, 44 g) and aqueous hydrochloric acid (1M, 107 mL) in ethanol (900 mL) is stirred at 60° until the mixture becomes homogeneous. The mixture is concentrated under reduced pressure in a stream of nitrogen. When the reaction volume reaches approximately half of the original volume, crystallization begins. The mixture is cooled to -10° for 3 hr and the title compound, is isolated by filtration, mp >260°; NMR (CDCl3) 7.88, 7.52, 7.28, 7.13, 4.86, 3.94-3.89, 3.62, 3.45, 3.15 and 2.01-1.96 δ.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure in a stream of nitrogen
  2. customhalf of the original volume, crystallization
  3. temperatureThe mixture is cooled to -10° for 3 hr

Sources & evidence

ORD record
ord-199952f5055741159255ff7ebe7f467f
Source dataset
uspto-grants-1998_08
Patent number
US05795986

Reaction notes

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