3-Chlorophenethylamine → HCID 11396083, compound

HRID 747982Notes

Reaction equation

HRID 747982 reaction equation
O=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([O:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=3)[CH:5]=[CH:4][C:3]1=2.[Cl:22][C:23]1[CH:24]=[C:25]([CH2:29][CH2:30][NH2:31])[CH:26]=[CH:27][CH:28]=1.[BH3-]C#N.[Na+]>Cl[Ti](Cl)(Cl)Cl>[Cl:22][C:23]1[CH:24]=[C:25]([CH2:29][CH2:30][NH:31][CH:2]2[CH2:11][CH2:10][CH2:9][C:8]3[CH:7]=[C:6]([O:12][C:13]4[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=4)[CH:5]=[CH:4][C:3]2=3)[CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 1393813-ChlorophenethylamineHCID 5003444Sodium cyanoborohydrideHCID 59750647HCID 59750647, compound2×

Product 1

HCID 11396083HCID 11396083, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

Using a method similar to Example 1, using 6-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-nicotinamide (Intermediate 2, 846 mg, 3.00 mmol), 2-(3-chlorophenyl)ethylamine (560 mg, 3.60 mmol), Ti(iPrO)4 (1.70 g, 6.00 mmol), TiCl4 (1.0M/DCM, 6.00 ml, 6.00 mmol), and NaBH3CN (377 mg, 6.00 mmol) gives the title compound (1.16 g) as a white solid. Mass spectrum (ion spray): m/z=422 (M+1); 1HNMR (CDCl3): 8.58 (s, 1H), 8.15 (d, 1H), 7.33 (d, 1H), 7.24-7.17 (m, 3H), 7.11 (d, 1H), 6.94 (d, 1H), 6.90 (d, 1H), 6.85 (s, 1H), 5.87 (br. s, 2H), 3.79 (t, 1H), 3.06-2.91 (m, 2H), 2.83-2.67 (m, 4H), 1.97-1.79 (m, 3H), 1.73 (m, 1H).

Sources & evidence

ORD record
ord-142e8835bce049ea8619a85af5a32d73
Source dataset
uspto-grants-2008_07
Patent number
US07399774B2

Reaction notes

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