Phenethylamine → 6-(3,3-Dimethyl-1-phenethylamino-indan-5-yloxy)-nicotinamide

HRID 422239Notes

Reaction equation

HRID 422239 reaction equation
[CH3:1][C:2]1([CH3:22])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][C:12]3[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=3)[CH:9]=2)[C:4](=O)[CH2:3]1.[CH2:23]([NH2:31])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[BH3-]C#N.[Na+]>Cl[Ti](Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:22])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][C:12]3[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=3)[CH:9]=2)[CH:4]([NH:31][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 5003444Sodium cyanoborohydrideHCID 597506546-(3,3-Dimethyl-1-oxo-indan-5-yloxy)-nicotinamide2×

Product 1

HCID 113730016-(3,3-Dimethyl-1-phenethylamino-indan-5-yloxy)-nicotinamideYield 66.5%

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

Using a method similar to Example 14, using 6-(3,3-dimethyl-1-oxo-indan-5-yloxy)-nicotinamide (Intermediate 11, 100 mg, 0.337 mmol), phenethylamine (49 mg, 0.405 mmol), Ti(iPrO)4 (192 mg, 0.675 mmol), TiCl4 (1.0M/DCM, 0.675 ml, 0.675 mmol), and NaBH3CN (42 mg, 0.675 mmol) gives the title compound (90 mg) as a white solid. Mass spectrum (ion spray): m/z=402 (M+1); 1HNMR (CDCl3): 8.60 (s, 1H), 8.14 (d, 1H), 7.32-7.19 (m, 6H), 6.95-6.88 (m, 3H), 6.25 (br. s, 2H), 4.31 (t, 1H), 3.02 (m, 2H), 2.86 (m, 2H), 2.33 (m, 1H), 1.68 (m, 3H), 1.31 (s, 3H), 1.17 (s, 3H).

Sources & evidence

ORD record
ord-89afc6a9a2bd40afaa399dc759cb78c2
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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