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

HRID 482320Notes

Reaction equation

HRID 482320 reaction equation
CS(O[CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[C:17]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[N:18][C:19]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:20][C:9]1=2)(=O)=O.[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>>[N:31]1([CH2:6][CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3[C:17]([N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[N:18][C:19]([N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[N:20][C:9]2=3)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 537324089-(2-Methanesulfonyloxyethyl)-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole

Product 1

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

Procedure

A mixture of 9-(2-methanesulfonyloxyethyl)-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole (IX, EXAMPLE4, 50 g) and piperidine (200 mL) is heated at reflux for 16 hr. Excess piperidine is removed under reduced pressure and the residue is partitioned between methylene chloride and aqueous sodium bicarbonate. The organic phase is washed with saline, dried over sodium sulfate and concentrated to give the title compound, NMR (CDCl3) 7.88, 7.28, 7.20, 7.10, 4.46-4.40, 3.94-3.90, 3.66-3.62, 2.74-2.68, 2.57, 1.98-1.94, 1.64-1.58 and 1.45 δ.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 16 hr
  3. customExcess piperidine is removed under reduced pressure
  4. customthe residue is partitioned between methylene chloride and aqueous sodium bicarbonate
  5. washThe organic phase is washed with saline
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7c48d4af53bd42ba93ee68291d14ed6a
Source dataset
uspto-grants-1998_08
Patent number
US05795986

Reaction notes

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