Piperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide → HCID 59885586, compound

HRID 720927Notes

Reaction equation

HRID 720927 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[O:22])[CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:29]1[CH2:31][C@@H:30]1[CH2:32][O:33][C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[N:37]=[CH:36][CH:35]=1>C(O)C>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][N:26]([CH2:31][C@@H:30]([OH:29])[CH2:32][O:33][C:34]3[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[N:37]=[CH:36][CH:35]=3)[CH2:25][CH2:24]2)=[O:22])[CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 12020260Piperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amideHCID 59885608HCID 59885608, compound

Product 1

HCID 59885586HCID 59885586, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Piperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide (4) (70.3 mg; 0.186 mmol) is dissolved in ethanol (10 mL) at ambient temperature. (R)-4-Oxiranylmethoxy-quinoline (91) (37.4 mg; 0.186 mmol) is added, then the mixture is refluxed for 22 hours. After cooling to ambient temperature, the solution is concentrated in vacuo at 40° C. The residue is purified via silica gel chromatography with gradient elution (50%→100% acetone in hexanes, then 5%→20% ethanol in acetone) affording the desired product (50 mg) as a yellow solid. ESMS: MH+580.4.

Workup

  1. temperaturethe mixture is refluxed for 22 hours
  2. concentrationthe solution is concentrated in vacuo at 40° C
  3. customThe residue is purified via silica gel chromatography with gradient elution (50%→100% acetone in hexanes

Sources & evidence

ORD record
ord-b56bf470c1c14a9dbd03e0444d4a4a57
Source dataset
uspto-grants-2006_11
Patent number
US07135483B2

Reaction notes

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