Sodium Iodide → (S)-3-tert-Butoxycarbonylamino-1,1-bis-[3-(3-methoxy-phenyl)-propyl]-piperidinium hydroxide

HRID 509906Notes

Reaction equation

HRID 509906 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1.[C:27](=[O:30])([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[OH-:5].[C:1]([O:5][C:6]([NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][N+:10]([CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:30][CH3:27])[CH:20]=2)([CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)[CH2:9]1)=[O:14])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 1388771-(3-Bromopropyl)-3-methoxybenzeneHCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamate

Product 1

HCID 117856455(S)-3-tert-Butoxycarbonylamino-1,1-bis-[3-(3-methoxy-phenyl)-propyl]-piperidinium hydroxide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-Piperidin-3-yl-carbamic acid tert-butyl ester (2.72 g, 13.6 mmol) and 1-(3-Bromo-propyl)-3-methoxy-benzene (6.6 g, 28.8 mmol), potassium carbonate (2.5 g, 18 mmol) and sodium iodide (4 g, 26.7 mmol) are dissolved in acetonitril (40 ml) and stirred at reflux for 1 day and the solvent is removed under vacuo. The residue is taken up in dichloromethane, filtered through a pad of silica, washed with a mixture of dichloromethane: methanol:conc.ammonia=4:1:0.1 and the filtrate is evaporated. LC (method L): tR=1.30 min; Mass spectrum (ESI+): m/z=497 [M]+.

Workup

  1. temperatureat reflux for 1 day
  2. customthe solvent is removed under vacuo
  3. filtrationfiltered through a pad of silica
  4. washwashed with a mixture of dichloromethane
  5. customammonia=4:1:0.1 and the filtrate is evaporated

Sources & evidence

ORD record
ord-b8040f7662784d95ac0e1c0337b03704
Source dataset
uspto-grants-2015_08
Patent number
US09096548B2

Reaction notes

Loading…