Potassium Iodide → Ammonia methanol

HRID 33701Notes

Reaction equation

HRID 33701 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:18]=[CH:17][C:9]([CH2:10][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:8][CH:7]=1.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(O)CCC.O>[NH3:11].[CH3:4][OH:5].[N:11]1([CH2:10][C:9]2[CH:17]=[CH:18][C:6]([O:5][CH2:4][CH2:3][CH2:2][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:7][CH:8]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 8082PiperidineHCID 10340Sodium CarbonateHCID 43659323-Chloropropyl 4-(piperidinomethyl)phenyl ether

Product 2

HCID 27663261-(3-(4-(1-Piperidinylmethyl)phenoxy)propyl)piperidineHCID 21705897Ammonia methanolYield 5%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

A solution of the product of Example 12 (6.13 g), piperidine (3.0 mL), sodium carbonate (3.6 g), and potassium iodide (190 mg) in n-butanol (50 mL) was heated to 105° C. for 21 h, cooled to RT, and treated with water (50 mL). The resulting mixture was extracted with DCM (4×50 mL), and the combined organic phases were dried (magnesium sulfate) and evaporated. Chromatography of the residue (5% 2M methanolic ammonia/methanol) gave the title compound as a waxy solid (3.2 g). 1H NMR (400 MHz, CDCl3): 7.19 (d, J=8.6 Hz, 2H), 6.83 (d, J=8.8 Hz, 2H), 3.97 (t, J=6.5 Hz, 2H), 3.4 (s, 2H), 2.48-2.31 (m, 10H), 2.00-1.92 (m, 2H), 1.62-1.52 (m, 8H), 1.47-1.38 (m, 4H).

Workup

  1. extractionThe resulting mixture was extracted with DCM (4×50 mL)
  2. dry with materialthe combined organic phases were dried (magnesium sulfate)
  3. customevaporated

Sources & evidence

ORD record
ord-a08c5bdb0a6f4983863ec5dec4cade4b
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Reaction notes

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