Potassium Carbonate → (E)-7-Methoxy-2-(4-(3-phenylpropenoyl)aminobutyl)-1,2,3,4-tetrahydroisoquinoline

HRID 1856793Notes

Reaction equation

HRID 1856793 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[C:13]([OH:23])(=O)/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:29]1[CH2:38][CH2:37][C:36]2[C:31](=[CH:32][C:33]([O:39][CH3:40])=[CH:34][CH:35]=2)[CH2:30]1.ON1C2C=CC=CC=2N=N1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:40][O:39][C:33]1[CH:32]=[C:31]2[C:36]([CH2:37][CH2:38][N:29]([CH2:28][CH2:27][CH2:26][CH2:25][NH:24][C:13](=[O:23])/[CH:14]=[CH:15]/[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:30]2)=[CH:35][CH:34]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 757711-HydroxybenzotriazoleHCID 444539Cinnamic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11075364HCID 11075364, compound

Product 1

HCID 9929021(E)-7-Methoxy-2-(4-(3-phenylpropenoyl)aminobutyl)-1,2,3,4-tetrahydroisoquinolineYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.41 g, 2.14 mmol) was added to a solution of trans-cinnamic acid (0.317 g, 2.14 mmol), 2-(4-aminobutyl)-7-methoxy-1,2,3,4-tetrahydroisoquinoline (0.5 g, 2.14 mmol) and 1-hydroxybenzotriazole (0.1 g, 0.7 mmol) in dichloromethane (8 ml). The mixture was shaken for 18 h, saturated aqueous potassium carbonate (5 ml) added and shaking continued for a further 1 h. The organic layer was chromatographed on silica gel using 10-100% ethyl acetate-hexane gradient elution to afford the title compound as a yellow gum (0.53 g, 68%).

Workup

  1. stirringshaking
  2. waitcontinued for a further 1 h
  3. customThe organic layer was chromatographed on silica gel using 10-100% ethyl acetate-hexane gradient elution

Sources & evidence

ORD record
ord-36d78281fea644c8bd9f9f25b07dcf36
Source dataset
uspto-grants-2000_11
Patent number
US06143762

Reaction notes

Loading…