Potassium Carbonate → N-(2-(1-benzylpiperidin-4-yl)ethyl)benzo[d]isoxazol-3-amine

HRID 2301201Notes

Reaction equation

HRID 2301201 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.[NH2:11][CH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[C:21]1([CH2:20][N:17]2[CH2:18][CH2:19][CH:14]([CH2:13][CH2:12][NH:11][C:2]3[C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=4[O:4][N:3]=3)[CH2:15][CH2:16]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18670022-(1-Benzylpiperidin-4-yl)ethan-1-amineHCID 27797803-Chloro-1,2-benzoxazole

Product 1

HCID 10449628N-(2-(1-benzylpiperidin-4-yl)ethyl)benzo[d]isoxazol-3-amineYield 15.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The procedure described in Example 21 was followed with 3-chloro-1,2-benzisoxazole (0.682 g, 4.44 mmol), 4-aminoethyl-1-phenylmethyl piperidine (0.970 g, 4.44 mmol), and K2CO3 (0.614 g, 4.44 mmol) in DMSO (30 mL). After purification, the title compound (0.231 g, 15%) was obtained as a pale yellow oil. 1H-NMR (CDCl3) δ 7.45-7.54 (m, 2H), 7.24-7.40 (m, 6H), 7.19 (t, 1H, J=7.8 Hz), 4.40 (brt, 1H, J=5.5 Hz), 3.52 (s, 2H), 3.45 (dt, 2H, J=7.4 Hz, J=6.0 Hz), 2.91 (brd, 2H, J=11.8 Hz), 1.99 (brt, 2H, J=11.2 Hz), 1.62-1.73 (m, 4H), 1.37-1.52 (m, 3H). 13C-NMR (CDCl3) δ 162.7, 158.6, 137.8, 129.8, 129.4, 128.2, 127.1, 122.1, 119.8, 116.3, 110.0, 63.3, 53.6, 41.5, 36.1, 33.4, 32.0. EIMS: 335 (M+), 244, 199, 186, 172, 91 (base). HRMS calc'd. for C21H25N3O: 335.1998. Found: 335.1909.

Workup

  1. customAfter purification

Sources & evidence

ORD record
ord-2c2da128ddd74fc7b2d2827e20819df6
Source dataset
uspto-grants-2002_12
Patent number
US06498255B2

Reaction notes

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