Water → HCID 57931190, compound

HRID 551146Notes

Reaction equation

HRID 551146 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([S:10]([N:13]1[CH2:18][CH2:17][C:16]([C:25]#[N:26])([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:15][CH2:14]1)(=[O:12])=[O:11])[CH2:8][CH3:9].O.[OH-].[Na+]>C(OCC)C>[CH2:7]([S:10]([N:13]1[CH2:18][CH2:17][C:16]([CH2:25][NH2:26])([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:15][CH2:14]1)(=[O:11])=[O:12])[CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57931197HCID 57931197, compound

Product 1

HCID 57931190HCID 57931190, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of lithium aluminium hydride in diethyl ether (1 M, 1.6 mL) at −78° C. was added a solution of 1′-(propylsulfonyl)-1,4′-bipiperidine-4′-carbonitrile (0.40 g, 1.34 mmol) in diethyl ether (10 mL) over 30 min. The mixture was stirred cold for 1 h then allowed to warm to room temperature and stirred for 2 h. The resultant mixture was cooled in an ice-bath and to the mixture was added water (0.17 mL), 15% NaOH solution (0.17 mL) then water (0.17 mL). The resultant white granular solid was filtered off and the filter-cake rinsed twice with diethyl ether. The filtrate was evaporated to give {[1′-(propylsulfonyl)-1,4′-bipiperidin-4′-yl]methyl}amine as a clear oil which was used in the next step without further purification; m/z (ES+) 304 (M++H).

Workup

  1. stirringstirred for 2 h
  2. filtrationThe resultant white granular solid was filtered off
  3. washthe filter-cake rinsed twice with diethyl ether
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-a45675908f4e4207bb36c4fd36301eb8
Source dataset
uspto-grants-2011_05
Patent number
US07947714B2

Reaction notes

Loading…