Isobutyraldehyde → HCID 21985214, compound

HRID 1157871Notes

Reaction equation

HRID 1157871 reaction equation
[CH:1](=O)[CH:2]([CH3:4])[CH3:3].[NH:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[CH2:15][N:16]([CH:26]1[C:35]2[N:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH2:29][CH2:28][CH2:27]1)[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][NH2:25])=[CH:20][CH:19]=1.[BH4-].[Na+]>CO>[CH2:1]([NH:25][CH2:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:16]([CH2:15][C:7]2[NH:6][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]=2)[CH:26]2[C:35]3[N:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH2:29][CH2:28][CH2:27]2)=[CH:19][CH:20]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6561IsobutyraldehydeHCID 4311764Sodium borohydrideHCID 21985008N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine

Product 1

HCID 21985214HCID 21985214, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Isobutyraldehyde (0.1 mL, 1.1 mmol) was condensed with N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (152 mg, 0.382 mmol) in dry CH3OH (5 mL) for 17 h and the resultant imine was reduced with NaBH4 (81 mg, 2.14 mmol) for 1 h (see General Procedures A and B). Purification of the crude product by radial chromatography (2 mm TLC plate, 50:1:1 CH2Cl2/CH3OH/NH4OH) gave the free amine (43 mg, 25%).

Workup

  1. customPurification of the crude product by radial chromatography (2 mm TLC plate, 50:1:1 CH2Cl2/CH3OH/NH4OH)

Sources & evidence

ORD record
ord-f69a4deb10be4d3f9664eeb809c575f0
Source dataset
uspto-grants-2010_10
Patent number
US07807694B2

Reaction notes

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