Triethylamine → HCID 22083371, compound

HRID 1242105Notes

Reaction equation

HRID 1242105 reaction equation
[CH2:1]([O:3][C:4]1([O:20][CH2:21][CH3:22])[CH2:9][CH2:8][N:7]([C@H:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:11])[C@@H:6]([CH2:18][NH2:19])[CH2:5]1)[CH3:2].C(N(CC)CC)C.C[O:31][C:32](=O)[C:33]1[C:38]([O:39][CH3:40])=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:41]Cl>C(#N)C>[CH3:40][O:39][C:38]1[CH:37]=[CH:36][CH:35]=[C:34]2[C:33]=1[C:32](=[O:31])[N:19]([CH2:18][C@H:6]1[CH2:5][C:4]([O:3][CH2:1][CH3:2])([O:20][CH2:21][CH3:22])[CH2:9][CH2:8][N:7]1[C@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:11])[CH2:41]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11162571HCID 11162571, compoundHCID 11687155HCID 11687155, compound

Product 1

HCID 22083371HCID 22083371, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

4,4-Diethoxy-1-((S)-1-phenyl-ethyl)-(R)-2-aminomethyl-piperidine (2.25 g, 7.37 mmol), and triethyl amine (1.49 g, 14.7 mmol) in acetonitrile (50 ml) was heated to 60° C. before 2-chlormethyl-6-methoxy-benzoic acid methyl ester (1.58 g, 7.37 mmol) in acetonitrile (25 ml) was added over the course of 1.5 hour. After addition the reaction mixture was stirred overnight at 60° C. The solvent was removed in vacuo and the residue was dissolved in dichloromethane (50 ml) and washed with saturated sodium bicarbonate. After drying (MgSO4), filtration and evaporation of the solvent in vacuo the residue was subjected to flash column chromatography (SiO2, ethyl acetate-light petrol ether (1:1)) to give 2.3 g (69%) of 2-(R)-(7-methoxy-2,3-dihydro-isoindol-1-one-2-ylmethyl)-4,4-diethoxy-1-(1-(S)-phenyl-ethyl)-piperidine.

Workup

  1. additionwas added over the course of 1.5 hour
  2. additionAfter addition the reaction mixture
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in dichloromethane (50 ml)
  5. washwashed with saturated sodium bicarbonate
  6. customAfter drying
  7. filtration(MgSO4), filtration and evaporation of the solvent in vacuo the residue

Sources & evidence

ORD record
ord-6c19bd1a8aad4093882ff0b6284ebce3
Source dataset
uspto-grants-2006_10
Patent number
US07115624B1

Reaction notes

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