Hydrochloric Acid → 4-[N-methyl-N-(3-cyclopropylmethylamino-2-pyridinyl) amino]piperidine

HRID 361835Notes

Reaction equation

HRID 361835 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:26])[C:15]2[C:20]([NH:21][CH2:22][CH:23]3[CH2:25][CH2:24]3)=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[CH3:26][N:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[C:15]1[C:20]([NH:21][CH2:22][CH:23]2[CH2:24][CH2:25]2)=[CH:19][CH:18]=[CH:17][N:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 107610091-tert-Butyloxycarbonyl-4-[N-methyl-N-(3-cyclopropylmethylamino-2-pyridinyl)amino]piperidine

Product 1

HCID 107538574-[N-methyl-N-(3-cyclopropylmethylamino-2-pyridinyl) amino]piperidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-tert-Butyloxycarbonyl-4-[N-methyl-N-(cyclopropylmethylamino-2-pyridinyl)amino]piperidine (EXAMPLE 161, 1.46 g, 4.05 mmol) is dissolved in 10 ml dioxane. Hydrochloric acid (30 ml of 4.0M in dioxane) is added. The solvent is removed by evaporation and the residue is suspended in water. The water is adjusted to pH=12 with sodium hydroxide (1N) and extracted with chloroform/methanol. The organic phase is dried over sodium sulfate and the solvent evaporated to give the title compound, NMR (300 MHz, CD3OD) 7.37, 6.77, 3.3-3.5, 2.85, 2.79, 2.45, 2.36, 1.53, 1.40, 0.92, 0.33 and 0.56δ.

Workup

  1. customThe solvent is removed by evaporation
  2. extractionextracted with chloroform/methanol
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-1416b9f47f9d4686a0d61019b7536ee7
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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