Potassium Carbonate → 1-[3-(1-Naphthoxy)-2-hydroxyprop-1-yl]-4-benzamidopiperidine

HRID 437227

Reaction equation

HRID 437227 reaction equation
[C:1]1([O:11][CH2:12][CH:13]([OH:16])[CH2:14]Cl)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:17]([NH:25][CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[C:1]1([O:11][CH2:12][CH:13]([OH:16])[CH2:14][N:29]2[CH2:30][CH2:31][CH:26]([NH:25][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:27][CH2:28]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 892761-Chloro-3-(1-naphthyloxy)-2-propanolHCID 118120N-4-Piperidylbenzamide

Product 1

HCID 214306471-[3-(1-Naphthoxy)-2-hydroxyprop-1-yl]-4-benzamidopiperidine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3-(α-Naphthoxy)-1-chloropropan-2-ol (1.18 g.) was refluxed for 16 hours in isopropyl alcohol (100 ml.) with 4-benzamidopiperidine (1.032 g.) and anhydrous potassium carbonate (1.037 g.). The mixture was filtered hot, cooled and evaporated to dryness. The gum so obtained gave the title compound as a solid on triturating in ether, m.p. 139°-141° C. (Found: C, 74.1; H, 7.1; N, 6.9. C25H28N2O3 requires C, 74.2; H, 7.0; N, 6.9%).

Workup

  1. filtrationThe mixture was filtered hot
  2. temperaturecooled
  3. customevaporated to dryness
  4. customThe gum so obtained

Sources & evidence

ORD record
ord-8fb03f6ffe34446b84c56e7af70e3b1a
Source dataset
uspto-grants-1977_06
Patent number
US04029801

Linked notes

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