Benzoyl chloride → HCID 49787504, compound

HRID 1020006Notes

Reaction equation

HRID 1020006 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([NH:18][C:19](=[O:23])[CH:20]([CH3:22])[CH3:21])[CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][NH:12][CH2:13]2.C(N(CC)CC)C.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CC(N(C)C)=O>[C:31]([N:12]1[CH2:11][CH2:10][C:9]2[C:14](=[CH:15][C:16]([NH:18][C:19](=[O:23])[CH:20]([CH3:21])[CH3:22])=[CH:17][C:8]=2[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH2:13]1)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 66611930HCID 66611930, compound

Product 1

HCID 49787504HCID 49787504, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

N-[5-(2-Chloro-phenyl)-1,2,3,4-tetrahydro-isoquinolin-7-yl]2-methylpropanamide (39 mgs, 0.12 mmoles) was dissolved in dimethylacetamide (1 ml) followed by the addition of triethylamine (20 ul, 0.144 mmoles) and finally benzoyl chloride (16.7 ul, 0.144 mmoles). The reaction was stirred at room temperature for 1.5 hours and purified by C18 reverse phase automated HPLC (14 mgs, 27% yield, 100% pure, CO-AAWO0025).

Workup

  1. custompurified by C18 reverse phase

Sources & evidence

ORD record
ord-4cac6f7a2a374781b9eed8044880fdeb
Source dataset
uspto-grants-2014_05
Patent number
US08716302B2

Reaction notes

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