Dicyclohexylcarbodiimide → HCID 14620589, compound

HRID 231821Notes

Reaction equation

HRID 231821 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23](O)=[O:24])[NH:8][CH2:7][CH2:6]2.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(#N)C>[CH3:14][O:13][C:12]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[CH2:6][CH2:7][N:8]3[C:23](=[O:24])[CH2:22][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[CH2:15][CH:9]3[C:10]=2[CH:11]=1

Participants

5

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 15152249HCID 15152249, compound

Product 1

HCID 14620589HCID 14620589, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To an ice-chilled solution of 2-[(1,2,3,4-tetrahydro-6,7-dimethoxyisoquinolinyl)methyl]benzeneacetic acid (XIc, Ex. 16) (0.4 g, 1.17 mmole) and 4-dimethylaminopyridine (0.15 g, 1.23 mmol) in dry acetonitrile (45 ml) was added with stirring dicyclohexylcarbodiimide (0.24 g, 1.17 mmole). The resulting mixture was stirred at room temperature for 6 hours, then heated to boiling briefly. When the mixture was cooled to room temperature, there was separated a precipitate which was removed by filtration. The filtrate was concentrated to about 10 ml, and chilled in ice to cause a separation of a precipitate. The precipitate was collected on a filter and recrystallized from ethanol, giving the titled product (0.26 g, 69%) which is identical with that described in Example 15.

Workup

  1. temperatureheated
  2. temperatureWhen the mixture was cooled to room temperature
  3. customthere was separated a precipitate which
  4. customwas removed by filtration
  5. concentrationThe filtrate was concentrated to about 10 ml
  6. temperaturechilled in ice
  7. customa separation of a precipitate
  8. customThe precipitate was collected on
  9. filtrationa filter
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-399e7d11f90d42aa8e971d61aab6e743
Source dataset
uspto-grants-1989_07
Patent number
US04849420

Reaction notes

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