Triethylamine → 1-[(5-Methyl-3-phenylisoxazol-4-yl)carbonyl]-4-phenylpiperidin-4-ol

HRID 1446290Notes

Reaction equation

HRID 1446290 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([OH:15])=O.[OH:16][C:17]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>ClCCl>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:3]=1[C:13]([N:20]1[CH2:19][CH2:18][C:17]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([OH:16])[CH2:22][CH2:21]1)=[O:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 143435-Methyl-3-phenylisoxazole-4-carboxylic acidHCID 963874-Phenylpiperidin-4-olHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 591700681-[(5-Methyl-3-phenylisoxazol-4-yl)carbonyl]-4-phenylpiperidin-4-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Methyl-3-phenylisooxazole-4-carboxylic acid (40 mg, 0.197 mmol), 4-hydroxy-4-phenylpiperidine (28.8 mg, 0.151 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (37.7 mg, 0.197 mmol) and triethylamine (59.8 mg, 0.591 mmol) were mixed in dichloromethane (2 mL) and stirred at room temperature over night. Solvent was evaporated in vacuo, and the residue was taken up in methanol (1 mL), filtered and purified by preparative chromatography. The combined fractions were partitioned between NaHCO3 (sat) and ethylacetate. The organic layer was washed with water and concentrated in vacuo to afford the title compound. HRMS (ESI, pos. ion) m/z calcd for C22H22N2O3: 362.1630, found 362.1627.

Workup

  1. customSolvent was evaporated in vacuo
  2. filtrationfiltered
  3. custompurified by preparative chromatography
  4. customThe combined fractions were partitioned between NaHCO3 (sat) and ethylacetate
  5. washThe organic layer was washed with water
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-15b361242f5f4ed8a60a748a5a0c5496
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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