2-Chlorobenzoxazole → HCID 15725118, compound

HRID 1990868Notes

Reaction equation

HRID 1990868 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[NH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1>CN(C=O)C>[CH2:21]([O:20][C:18]([N:15]1[CH2:14][CH2:13][CH:12]([NH:11][C:2]2[O:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)[CH2:17][CH2:16]1)=[O:19])[CH3:22]

Participants

4

Reactant 2

HCID 119862-ChlorobenzoxazoleHCID 100867Ethyl 4-amino-1-piperidinecarboxylate

Product 1

HCID 15725118HCID 15725118, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloro-benzooxazole (8.00 g, 52.1 mmol, 1.0 equiv) and ethyl 4-amino-1-piperidine carboxylate (10.78 g, 62.5 mmol, 1.2 equiv) in anhydrous DMF (50 mL) was stirred at rt. A precipitate formed over night which was filtered off, the volume of the filtrate reduced and the residue taken up in ethyl acetate (10 mL). Precipitation of this solution from hexane provided an additional batch of the title compound as a white solid. Combined yield: 6.8 g (45%). 1H NMR (400 MHz, CDCl3): δ 1.27 (t, J=7.2 Hz, 3H), 1.48-1.52 (m, 2H), 2.14-2.18 (m, 2H), 3.09 (br t, 2H), 3.81-3.95 (m, 1H), 4.12-4.18 (m, 2H), 4.15 (q, J=7.2 Hz, 2H), 5.64 (br d, J=7.8 Hz, 1H), 7.04 (t, J=7.8 Hz, 1H), 7.17 (t, J=7.6 Hz, 1H), 7.25 (d, J=7.8 Hz, 1H), 7.36 (d, J=7.6 Hz, 1H). 13C NMR (100 MHz, CDCl3): δ 14.93, 32.53, 42.85, 50.66, 61.72, 109.00, 116.62, 121.24, 124.24, 143.10, 148.66, 155.72, 161.32. MS (ISP): 290.0 [M+H]+.

Workup

  1. customA precipitate formed over night which
  2. filtrationwas filtered off
  3. customPrecipitation of this solution from hexane

Sources & evidence

ORD record
ord-c21efa09d1fe42cca2cf4e93a16924b2
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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