Dicyclohexylcarbodiimide → 1,2,3,4-Tetrahydro-6-methoxy-N-3-(2-thienyl)propionylisoquinoline

HRID 1088695Notes

Reaction equation

HRID 1088695 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2.O.OC1C2N=NNC=2C=CC=1.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[CH2:29][CH2:30][C:31](O)=[O:32].C1CCC(N=C=NC2CCCCC2)CC1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:31](=[O:32])[CH2:30][CH2:29][C:25]1[S:24][CH:28]=[CH:27][CH:26]=1)[CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinolineHCID 7031693-(2-Thienyl)propanoic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 157186901,2,3,4-Tetrahydro-6-methoxy-N-3-(2-thienyl)propionylisoquinolineYield 74.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,2,3,4-tetrahydro-6-methoxyisoquinoline (3.29 g), hydroxybenzotriazole monohydrate (5.72 g) and 3-(2-thienyl)propanoic acid (3.31 g) in 280 ml of dry tetrahydrofuran (THF) at 0° C. was added DCC (4.37 g) in one portion. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was filtered and concentrated. The residue was taken up into 200 ml of ethyl acetate (EtOAc) refiltered, washed with 5% aq. HCl (50 ml), 5% aq. NaCl (50 ml), 10% aq. KOH (50 ml), dried (MgSO4), filtered, and concentrated. Chromatography on silica gel (elution with 20% EtOAc:hexanes) afforded 4.54 g of the desired product.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. washwashed with 5% aq. HCl (50 ml), 5% aq. NaCl (50 ml), 10% aq. KOH (50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3e5072f731db4fcb96a87b0bdc848440
Source dataset
uspto-grants-1990_10
Patent number
US04963563

Reaction notes

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