Hydrochloric Acid → 4,4-dimethyl-1,4-azasilinane hydrochloride

HRID 590543Notes

Reaction equation

HRID 590543 reaction equation
C([N:8]1[CH2:13][CH2:12][Si:11]([CH3:15])([CH3:14])[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:16]>CCO>[ClH:16].[CH3:14][Si:11]1([CH3:15])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69344008HCID 69344008, compound

Product 1

HCID 672158374,4-dimethyl-1,4-azasilinane hydrochlorideYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4,4-dimethyl-1,4-azasilinane 3 (2.3 g, 10.5 mmol) in EtOH (20 mL), 6N hydrochloricacid (1.75 mL, 10.5 mmol) is added and the solvent is removed under reduced pressure. The reaction mixture is co-evaporated with EtOH (2×10 mL) and recrystallized from EtOH-diethyl ether. To a slurry of Pd/C (50 mg) in EtOH (15 mL) an ethanolic solution of above prepared HCl salt is added drop wise and stirred at 25° C. under hydrogen atmosphere for 20 h. The reaction mixture is filtered through celite and washed with 2×20 mL of MeOH. The filtrate is then concentrated under reduced pressure to give viscous oil which was triturated with diethyl ether to obtain the product 4 as a white solid (950 mg) in 70% yield.

Workup

  1. customthe solvent is removed under reduced pressure
  2. customrecrystallized from EtOH-diethyl ether
  3. customTo a slurry of Pd/C (50 mg) in EtOH (15 mL) an ethanolic solution of above prepared HCl salt
  4. additionis added drop wise
  5. filtrationThe reaction mixture is filtered through celite
  6. washwashed with 2×20 mL of MeOH
  7. concentrationThe filtrate is then concentrated under reduced pressure
  8. customto give viscous oil which
  9. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-6ddc01f2f212416aa55a37acea05efc5
Source dataset
uspto-grants-2016_01
Patent number
US09233989B2

Reaction notes

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