Triethylamine → HCID 14851351, compound

HRID 1461724Notes

Reaction equation

HRID 1461724 reaction equation
[CH2:1]1[CH:6]([C:7]([OH:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:4][NH:3][CH2:2]1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][Cl:27].C(N(CC)CC)C>C1COCC1>[ClH:27].[OH:20][C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:6]1[CH2:5][CH2:4][N:3]([CH2:26][C:25]2[CH:28]=[CH:29][CH:30]=[C:23]([O:22][CH3:21])[CH:24]=2)[CH2:2][CH2:1]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15723AzacyclonolHCID 699943-Methoxybenzyl chloride

Product 1

HCID 14851351HCID 14851351, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 8.0 g (30 mmol) of α,α-diphenyl-4-piperidinomethanol, 2.35 g (15 mmol) of 3-methoxybenzyl chloride, 0.5 g of triethylamine and 30 ml of THF is stirred under reflux for 1 hour, during which a colorless precipitate separates out. After cooling to 20° C., the precipitate is filtered off, and the filtrate is concentrated. For working up, the residue is taken up in 5 ml of methylene chloride, and ethereal HCl solution is added until no further precipitation occurs. The mixture is diluted with 30 ml of methylene chloride, the precipitate is filtered, and the filtrate is concentrated. Drying of the oily residue at 40° C. in vacuo results in 6.5 g of final product. Decomposition point about 80° C. Characteristic IR bands: 3360, 1590, 1480, 1438, 1256, 690 cm.

Workup

  1. temperatureunder reflux for 1 hour, during which a colorless precipitate
  2. filtrationthe precipitate is filtered off
  3. concentrationthe filtrate is concentrated
  4. additionethereal HCl solution is added until no further precipitation
  5. additionThe mixture is diluted with 30 ml of methylene chloride
  6. filtrationthe precipitate is filtered
  7. concentrationthe filtrate is concentrated
  8. customDrying of the oily residue at 40° C. in vacuo

Sources & evidence

ORD record
ord-8c3b903e8ed64d9ab6549ed108c9bed6
Source dataset
uspto-grants-1991_12
Patent number
US05077301

Reaction notes

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