Sodium Chloride → HCID 68699883, compound

HRID 1990869Notes

Reaction equation

HRID 1990869 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](S)=[N:7][C:6]=2[CH:11]=1.[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1.[Cl-].[Na+]>CC(N(C)C)=O>[CH2:22]([O:21][C:19]([N:16]1[CH2:15][CH2:14][CH:13]([NH:12][C:8]2[O:9][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:11][C:6]=3[N:7]=2)[CH2:18][CH2:17]1)=[O:20])[CH3:23]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 178527795HCID 178527795, compound

Product 1

HCID 68699883HCID 68699883, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 5-chloro-benzooxazole-2-thiol (4.00 g, 21.5 mmol, 1.0 equiv; commercially available from Aldrich) and ethyl 4-amino-1-piperidine carboxylate (4.9 g, 28.0 mmol, 1.3 equiv) in anhydrous DMAc (5 mL) was heated to 200° C. under microwave irradiation for 20 min. To the crude reaction mixture was added a conc. solution of sodium chloride (100 mL), the solution extracted with ethyl acetate (3×100 mL) and the combined organic phases dried over MgSO4. Purification of the crude material with column chromatography on silica eluting with hexane/ethyl acetate (2:1→1:1) yielded 2.7 g (39%) of the title compound. 1H NMR (400 MHz, DMSO): δ 1.19 (t, J=7.1 Hz, 3H), 1.39-1.45 (m, 2H), 1.93-1.97 (m, 2H), 2.98 (br s, 2H), 3.77-3.78 (m, 1H), 3.91-3.95 (m, 2H), 4.04 (q, J=7.1 Hz, 2H), 7.00 (dd, J=8.4 Hz, J=2.1 Hz, 1H), 7.29 (d, J=2.1 Hz, 1H), 7.36 (d, J=8.4 Hz, 1H), 8.19 (d, J=7.6 Hz, 1H). 13C NMR (100 MHz, DMSO): δ 14.53, 31.11, 42.07, 49.60, 60.63, 109.45, 115.10, 119.65, 127.78, 144.86, 146.71, 154.56, 162.50. MS (ISP): 324.1 [M+H]+.

Workup

  1. customTo the crude reaction mixture
  2. extractionthe solution extracted with ethyl acetate (3×100 mL)
  3. dry with materialthe combined organic phases dried over MgSO4
  4. customPurification of the crude material with column chromatography on silica eluting with hexane/ethyl acetate (2:1→1:1)

Sources & evidence

ORD record
ord-3c9761cf4e48427d88550cb04bccfdce
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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