Hydrochloric Acid → HCID 20343067, compound

HRID 2050046Notes

Reaction equation

HRID 2050046 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH3:5].[CH2:6]([NH-:11])[CH2:7][CH:8]([CH3:10])[CH3:9].Cl>O1CCCC1.CO>[CH2:6]([NH:11][CH2:5][CH2:4][CH2:3][S:2][CH3:1])[CH2:7][CH:8]([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86736948HCID 86736948, compound

Product 1

HCID 20343067HCID 20343067, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The amide from (a) (1.9 g) in tetrahydrofuran (20 ml) was treated under nitrogen at 0° with boranetetrahydrofuran complex (1 Molar in tetrahydrofuran 20 ml) and stirred overnight. 2 Molar hydrogen chloride in methanol (20 ml) was added and the mixture was boiled for 30 minutes, evaporated and the residue partitioned between ethyl acetate and water. The aqueous layer was basified and extracted with ether. The dried extract was evaporated to give the amine an oil (1.6 g). Rf3A=0.72, Rf7B=0.63, Rf4A=0.74

Workup

  1. waitthe mixture was boiled for 30 minutes
  2. customevaporated
  3. customthe residue partitioned between ethyl acetate and water
  4. extractionextracted with ether
  5. extractionThe dried extract
  6. customwas evaporated

Sources & evidence

ORD record
ord-6ceb04e61dcf4bad93f647e53046f961
Source dataset
uspto-grants-1980_04
Patent number
US04199568

Reaction notes

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