Dicyclohexylcarbodiimide → HCID 22168000, compound

HRID 1031613Notes

Reaction equation

HRID 1031613 reaction equation
[N:1]1([CH2:6][CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[CH2:10][CH2:9][NH:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.N1(CC2C3C(=CC(OC)=CC=3)CCN2)CCCC1.[Cl:37][C:38]1[CH:39]=[C:40]([CH2:45][C:46](O)=[O:47])[CH:41]=[CH:42][C:43]=1[Cl:44].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.C(OCC)(=O)C>[ClH:37].[N:1]1([CH2:6][C:7]2([C:46](=[O:47])[CH2:45][C:40]3[CH:41]=[CH:42][C:43]([Cl:44])=[C:38]([Cl:37])[CH:39]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[CH2:10][CH2:9][NH:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 798743,4-Dichlorophenylacetic acidHCID 15005444HCID 15005444, compoundHCID 22168089HCID 22168089, compound

Product 1

HCID 22168000HCID 22168000, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Prepared as Ex. No. 1, from 4.3 g (17.48 mmoles) of a mixture containing 1-(pyrrolidin-1-yl)methyl-8-methoxy-1,2,3,4-tetrahydroisoquinoline and 1-(pyrrolidin-1-yl)methyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline, 4.3 g (20.98 mmoles) of 3,4-dichlorophenylacetic acid, and 8.0 g (38.80 mmoles) of dicyclohexylcarbodiimide, in 110 ml of dry methylene chloride. The silica gel chromatographic column was eluted with CH2Cl2, containing increasing amounts of MeOH (0.6-2.5%); 1.5 g of the crude product were obtained and dissolved in 40 ml of ethyl acetate. The solution was brought to acidic pH with HCl/diethyl ehter and the precipitate filtered, washed and dried, to yield 1.2 g of the title compound.

Workup

  1. customPrepared as Ex
  2. washThe silica gel chromatographic column was eluted with CH2Cl2
  3. additioncontaining
  4. temperatureincreasing amounts of MeOH (0.6-2.5%)
  5. custom1.5 g of the crude product were obtained
  6. filtrationthe precipitate filtered
  7. washwashed
  8. customdried

Sources & evidence

ORD record
ord-b77a218ed8794188b6a7e299b3d44668
Source dataset
uspto-grants-1990_09
Patent number
US04954509

Reaction notes

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