Ethyl 4-amino-1-piperidinecarboxylate → HCID 68699686, compound

HRID 1990880Notes

Reaction equation

HRID 1990880 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[O:12][C:11](Cl)=[N:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[NH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH2:17]1>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[C:13]2[O:12][C:11]([NH:15][CH:16]3[CH2:17][CH2:18][N:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:20][CH2:21]3)=[N:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 68406054Methyl 2-chloro-1,3-benzoxazole-7-carboxylate

Product 1

HCID 68699686HCID 68699686, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-benzooxazole-7-carboxylic acid methyl ester (0.43 g, 2.05 mmol, 1.0 equiv) in acetonitrile (30 mL) was added ethyl 4-amino-1-piperidine carboxylate (0.64 g, 3.08 mmol, 1.5 equiv) and the reaction mixture heated to reflux for 30 min. The solvent was removed under reduced pressure and the crude material purified with column chromatography on silica eluting with dichloromethane/methanol (4:1) to afforded 0.68 g (95%) of the title compound. 1H NMR (300 MHz, DMSO): δ 1.19 (t, J=7.0 Hz, 3H), 1.38-1.51 (m, 2H), 1.95-2.00 (m, 2H), 2.96-3.03 (m, 2H), 3.78-3.81 (m, 1H), 3.89 (s, 3H), 3.82-3.96 (m, 2H), 4.04 (q, J=7.0 Hz, 2H), 7.23 (t, J=7.9 Hz, 1H), 7.50 (dd, J=7.9 Hz, J=1.9 Hz, 2H), 8.34 (d, J=7.3 Hz, 2H). 13C NMR (75 MHz, DMSO): δ 14.54, 31.01, 42.04, 49.71, 52.05, 60.63, 112.36, 119.98, 121.27, 123.51, 144.77, 147.00, 154.57, 162.13, 164.17. MS (ISP): 347.9 [M+H]+.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 30 min
  3. customThe solvent was removed under reduced pressure
  4. customthe crude material purified with column chromatography on silica eluting with dichloromethane/methanol (4:1)

Sources & evidence

ORD record
ord-f076ad4bcd7d4c9bb8562b790a2ff017
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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