Acetic Acid → HCID 178519690, compound

HRID 983637Notes

Reaction equation

HRID 983637 reaction equation
C[O:2][C:3]1C=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:11])C.[NH:12]1C2C=CC=CC=2N=C1CN(C1C2N=CC=CC=2CCC1)CC1C=CC(CN)=CC=1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1>[OH:2][C:3]1[C:4]([CH:9]=[O:11])=[CH:5][CH:6]=[CH:7][N:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 684812'-MethoxyacetophenoneHCID 5049666Sodium triacetoxyborohydrideHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine

Product 1

HCID 178519690HCID 178519690, compoundYield 134.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(2-methoxy-phenyl)-ethanone (69 μL, 0.50 mmol), N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (200 mg, 0.50 mmol) and AcOH (0.10 mL, 1.4 mmol) in THF (5 mL) was added NaBH(OAc)3 and the mixture was stirred at room temperature for 48 hours. Purification of the crude light yellow foam to (267 mg) by column chromatography on silica gel (100:1:1-CH2Cl2:MeOH:NH4OH) followed by radial chromatography on silica gel (100:1:1-CH2Cl2:MeOH:NH4OH) afforded the desired product (83 mg, 27%) as a white foam.

Workup

  1. customPurification of the crude light yellow foam to (267 mg) by column chromatography on silica gel (100:1:1-CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-410d033c25f94fbc885c129994d06d78
Source dataset
uspto-grants-2005_03
Patent number
US06864265B2

Reaction notes

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