Methylamine → 171049-43-7

HRID 2301192Notes

Reaction equation

HRID 2301192 reaction equation
I[CH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.[CH3:18][NH2:19]>C1COCC1>[CH3:18][NH:19][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 9975355Tert-butyl 4-(3-iodopropyl)piperidine-1-carboxylate

Product 1

HCID 18374734171049-43-7Yield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(3-iodoprop-1-yl)-1-tert-butoxycarbonyl-piperidine (728 mg, 2.06 mmol,) in 5.0 mL of THF was treated with 5.0 mL of methylamine (70% in water) and the resulting mixture was stirred at rt for 18 h. The mixture was partitioned between diethyl ether (50 mL) and water (50 mL) and the layers were separated. The organic layer was washed with 50 mL of sat'd NaCl, dried and concentrated to afford 457 mg (83%) of the title compound: 1H NMR (500 MHz, CDCl3): δ 1.05-1.68 (19H), 1.47 (s, 9H), 2.45 (s, 3H), 2.56-2.68 (4H), 4.00-4.15 (2H).

Workup

  1. customThe mixture was partitioned between diethyl ether (50 mL) and water (50 mL)
  2. customthe layers were separated
  3. washThe organic layer was washed with 50 mL of sat'd NaCl
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-454fd118935e44be8dfdb918ebb27eb0
Source dataset
uspto-grants-2002_12
Patent number
US06498161B1

Reaction notes

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