Hydrochloric Acid → HCID 59569874, compound

HRID 2071057Notes

Reaction equation

HRID 2071057 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([N:12]([CH3:17])[S:13]([CH3:16])(=[O:15])=[O:14])[CH:6]=[C:7]([C:9]([CH3:11])=[CH2:10])[CH:8]=1.[BH4-].[Na+].Cl>CCO.C1COCC1>[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([N:12]([CH3:17])[S:13]([CH3:16])(=[O:15])=[O:14])[CH:6]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 68670509HCID 68670509, compound

Product 1

HCID 59569874HCID 59569874, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of crude N-(3-(aminomethyl)-5-(prop-1-en-2-yl)phenyl)-N-methylmethanesulfonamide and 68.3 mg (0.2871 mmol) of CoCl2.6H2O in 3 mL of EtOH and 1 mL of THF at 50° C. was added 0.169 g of NaBH4 in 2 portions. After the mixture was stirred for about 3.5 h, 5 N HCl was added to a pH=1. The mixture was concentrated and (28-30) % NH4OH solution was added to pH=8. The aqueous layer was extracted with the extract of (40 mL of CHCl3: 5 mL of H2O: 5 mL of MeOH) (3×). The combined extracts were dried over Na2SO4, filtered, and concentrated. N-(3-(aminomethyl)-5-isopropylphenyl)-N-methylmethanesulfonamide was used in the next reaction without further purification.

Workup

  1. concentrationThe mixture was concentrated
  2. addition(28-30) % NH4OH solution was added to pH=8
  3. extractionThe aqueous layer was extracted with the
  4. extractionextract of (40 mL of CHCl3: 5 mL of H2O: 5 mL of MeOH) (3×)
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customN-(3-(aminomethyl)-5-isopropylphenyl)-N-methylmethanesulfonamide was used in the next reaction without further purification

Sources & evidence

ORD record
ord-9cfe862ad7714acf857c7250e3ab28b3
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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