Potassium Carbonate → 2-(4-(4-(3Cyanophenyl)benzoylamino)butyl)-7-methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 1003707Notes

Reaction equation

HRID 1003707 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[NH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][C:22]([O:28][CH3:29])=[CH:23][CH:24]=2)[CH2:19]1.[C:30]([C:32]1[CH:33]=[C:34]([C:38]2[CH:46]=[CH:45][C:41]([C:42](O)=[O:43])=[CH:40][CH:39]=2)[CH:35]=[CH:36][CH:37]=1)#[N:31].ON1C2C=CC=CC=2N=N1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:30]([C:32]1[CH:33]=[C:34]([C:38]2[CH:39]=[CH:40][C:41]([C:42]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:27][CH2:26][C:25]4[C:20](=[CH:21][C:22]([O:28][CH3:29])=[CH:23][CH:24]=4)[CH2:19]3)=[O:43])=[CH:45][CH:46]=2)[CH:35]=[CH:36][CH:37]=1)#[N:31]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27579514-(3-cyanophenyl)benzoic AcidHCID 11075364HCID 11075364, compound

Product 1

HCID 187970152-(4-(4-(3Cyanophenyl)benzoylamino)butyl)-7-methoxy-1,2,3,4-tetrahydroisoquinolineYield 61%

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 2-(4-aminobutyl)-7-methoxy-1,2,3,4-tetrahydroisoquinoline (0.5 g, 2.14 mmol), 4-(3-cyanophenyl)benzoic acid (0.368 g, 2.14 mmol) and 1-hydroxybenzotriazole (0.1 g, 0.7 mmol) in dichloromethane (8 ml). The resultant mixture was shaken for 18 h. before saturated aqueous potassium carbonate (5 ml) was added and shaking continued 1 hr. 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 (0.57 g, 61%).

Workup

  1. additionwas added
  2. customThe organic layer was chromatographed on silica gel using 10-100% ethyl acetate-hexane gradient elution

Sources & evidence

ORD record
ord-29e37f0a0e2c4120b3f9a847907fdc1b
Source dataset
uspto-grants-2000_04
Patent number
US06046210

Reaction notes

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