4-Piperidineethanol → HCID 13336380, compound

HRID 1788740Notes

Reaction equation

HRID 1788740 reaction equation
[C:1]1([C:7]2[N:16]=[C:15]([C:17]([O:19]CC)=O)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][OH:30])[CH2:24][CH2:23]1>O>[C:1]1([C:7]2[N:16]=[C:15]([C:17]([N:22]3[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][OH:30])[CH2:24][CH2:23]3)=[O:19])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 739534-PiperidineethanolHCID 20158356HCID 20158356, compound

Product 1

HCID 13336380HCID 13336380, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-phenylquinazoline-4-carboxylate (1.7 g) and piperidine-4-ethanol (8 g) are heated at 150° C. for 4 hours. After cooling, water is added and the mixture is extracted with ethyl acetate. The organic phase is dried over magnesium sulphate and evaporated to dryness under reduced pressure. The residue is chromatographed on silica gel with ethyl acetate as the eluant, and the product recovered is recrystallised from isopropyl ether. This gives 1-[(2-phenylquinazoline-4-yl)carbonyl]-piperidine-4-ethanol (0.5 g), melting at 146° C.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture is extracted with ethyl acetate
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. customevaporated to dryness under reduced pressure
  5. customThe residue is chromatographed on silica gel with ethyl acetate as the eluant
  6. customthe product recovered
  7. customis recrystallised from isopropyl ether

Sources & evidence

ORD record
ord-dadf8d7dde1b4f6bbc1fb4ee0a4ec3a0
Source dataset
uspto-grants-1987_08
Patent number
US04684652

Reaction notes

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