Hydrochloric Acid → 3-(Piperidin-1-ylmethyl)benzenethiol

HRID 1719211Notes

Reaction equation

HRID 1719211 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].NC1C(=O)C(=O)C=1NCC[S:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:19]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.Cl.[OH-].[NH4+]>CCOCC.O>[N:25]1([CH2:24][C:20]2[CH:19]=[C:18]([SH:17])[CH:23]=[CH:22][CH:21]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 24436Sodium SulfateHCID 13505506HCID 13505506, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 135055073-(Piperidin-1-ylmethyl)benzenethiolYield 180.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminum hydride (45.3 g, 1.19 moles) in 2200 mL of ether was added, dropwise under nitrogen, a solution of dithio bis-3,3'-N,N-di(piperidino)benzenecarboxamide (141.5 g, 0.32 mole) [prepared in Step B] in 2200 mL of ether and the mixture was stirred at ambient temperature for 20 hours. The mixture was decomposed by the addition of saturated sodium sulfate solution and filtered. The filter cake was stirred with 3000 mL of water and a solution of citric acid monohydrate (550 g, 2.62 moles) in 550 mL of water was added. The pH of the solution was adjusted to about 2 with 12N HCl and then to pH 8 with concentrated ammonium hydroxide. The solution was exhaustively extracted with ether to yield 120 g of product.

Workup

  1. additionwas added, dropwise under nitrogen
  2. filtrationfiltered
  3. extractionThe solution was exhaustively extracted with ether

Sources & evidence

ORD record
ord-7ae14b2e6c4c4af384e63ed66f8e6f2f
Source dataset
uspto-grants-1985_09
Patent number
US04539316

Reaction notes

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