1-Carbethoxy-4-dimethylamino-3-methylpiperidine → N,N,3-trimethylpiperidin-4-amine

HRID 1865229Notes

Reaction equation

C([N:6]1[CH2:11][CH2:10][CH:9]([N:12]([CH3:14])[CH3:13])[CH:8]([CH3:15])[CH2:7]1)(OCC)=O>[OH-].[Na+]>[CH3:13][N:12]([CH3:14])[CH:9]1[CH2:10][CH2:11][NH:6][CH2:7][CH:8]1[CH3:15]

Participants

Conditions

Temperature: 110 °C

Procedure

1-Carbethoxy-4-dimethylamino-3-methylpiperidine (3.5 g, 16.3 mmol) was suspended in 5 M NaOH solution (20 ml), stirred at 110° C. for 48 hr, cooled, extracted with ethyl acetate, dried (Na2SO4) and concentrated to dryness to afford 4-dimethylamino-3-methylpiperidine. Yield 1.0 g (43%), C8H18N2, m/z 143 (M+1), PMR (CDCl3): 0.96 (dd, 3H), 1.3 (m, 1H), 1.5 (m, 1H), 1.74 (m, 1H), 2.08 (m, 1H), 2.24 (s, 6H), 2.38 (m, 1H), 2.61 (bs, 1H, D2O exchangeable), 2.86 (m, 1H), 3.16 (m, 1H), 3.68 (m, 1H).

Workup

temperaturecooled
extractionextracted with ethyl acetate
dry with materialdried (Na2SO4)
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-04df2f07ee314613a6ea6b4ed362a47c
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07626032B2

Reaction notes

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