Piperidine → 4-[3-(3-Piperidin-1-yl-propoxy)-isoxazol-5-ylmethyl]-piperidine

HRID 30486Notes

Reaction equation

HRID 30486 reaction equation
Cl[CH2:2][C:3]1[O:7][N:6]=[C:5]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:4]=1.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(Cl)Cl>[N:12]1([CH2:11][CH2:10][CH2:9][O:8][C:5]2[CH:4]=[C:3]([CH2:2][CH:21]3[CH2:22][CH2:23][NH:18][CH2:19][CH2:20]3)[O:7][N:6]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 671892741-[3-(5-Chloromethyl-isoxazol-3-yloxy)-propyl]-piperidine

Product 1

HCID 446221604-[3-(3-Piperidin-1-yl-propoxy)-isoxazol-5-ylmethyl]-piperidineYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[3-(5-Chloromethyl-isoxazol-3-yloxy)-propyl]-piperidine (0.15 g, 0.80 mmol) was dissolved in DCM (5 mL) and piperidine (0.24 mL, 2.4 mmol) was added slowly. The reaction mixture was stirred overnight at rt and then was concentrated to yield the crude product (0.140 g). The crude product was purified (SiO2: 0-5% 2 M NH3 in MeOH/DCM) to give the final product (0.118 g, 47.6%). MS (ESI): exact mass calcd. for C17H29N3O2, 307.23; m/z found 308.4 [M+H]+. 1H NMR (500 MHz, CDCl3): 5.75 (s, 1H), 4.25-4.20 (m, 2H), 3.53 (s, 2H), 2.47-2.31 (m, 10H), 1.98-1.90 (m, 2H), 1.61-1.52 (m, 8H), 1.45-1.35 (m, 4H).

Workup

  1. concentrationwas concentrated
  2. customto yield the crude product (0.140 g)
  3. customThe crude product was purified (SiO2: 0-5% 2 M NH3 in MeOH/DCM)

Sources & evidence

ORD record
ord-19f1fe01c2814fc19ddfc1b7a34455c7
Source dataset
uspto-grants-2008_09
Patent number
US07423147B2

Reaction notes

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