Hydrochloric Acid → 5-(2,2,4-Trimethyl-piperazin-1-ylmethyl)-pyridin-2-ylamine

HRID 43145

Reaction equation

HRID 43145 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][C:16]2([CH3:23])[CH3:22])=[CH:10][N:9]=1)(C)(C)C.Cl>O1CCOCC1.CO>[CH3:22][C:16]1([CH3:23])[CH2:17][N:18]([CH3:21])[CH2:19][CH2:20][N:15]1[CH2:14][C:11]1[CH:12]=[CH:13][C:8]([NH2:7])=[N:9][CH:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66914640[5-(2,2,4-Trimethyl-piperazin-1-ylmethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

Product 1

HCID 669146025-(2,2,4-Trimethyl-piperazin-1-ylmethyl)-pyridin-2-ylamineYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of [5-(2,2,4-trimethyl-piperazin-1-ylmethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (Step 110.2) (1.94 g, 5.8 mmol), a 4 N solution of HCl in dioxane (20 mL) and MeOH (5 mL) was stirred for 12 h at it and concentrated. The residue was purified by silica gel column chromatography (DCM/NH3aq, 99:1→DCM/MeOH/NH3aq, 95:4:1) to afford 1.02 g of the title compound as a white solid. Title compound: ESI-MS: 235.2 [M+H]+; TLC: Rf=0.11 (DCM/MeOH, 9:1).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel column chromatography (DCM/NH3aq, 99:1→DCM/MeOH/NH3aq, 95:4:1)

Sources & evidence

ORD record
ord-15150eafde074e36bfe09ca264bc2d6b
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Linked notes

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