Hydrochloric Acid → (R)-4-(3,4-dichlorophenyl)butan-2-amine hydrochloride

HRID 1844422Notes

Reaction equation

HRID 1844422 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C@H:11]([NH:13][S@](C(C)(C)C)=O)[CH3:12])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.CC(S(OC)=O)(C)C>CO.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C@H:11]([NH2:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 543690Methyl 2-methylpropane-2-sulfinateHCID 86731088(S)-N-((R)-4-(3,4-dichlorophenyl)butan-2-yl)-2-methylpropane-2-sulfinamide

Product 1

HCID 86731090(R)-4-(3,4-dichlorophenyl)butan-2-amine hydrochlorideYield 195%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

(S)-N-((R)-4-(3,4-Dichlorophenyl)butan-2-yl)-2-methylpropane-2-sulfinamide (600 mg, 1.862 mmol) was stirred in MeOH (10 mL) at rt. 4N HCl in dioxane (5 mL) was added. The resulting mixture was stirred at rt for 20 min. The solvents were evaporated and CH2Cl2 (3×) was added and evaporated. The resulting white solids were vacuum dried for 5 h to give (R)-4-(3,4-dichlorophenyl)butan-2-amine hydrochloride (462 mg, 1.815 mmol, 97% yield) as off-white solids and methyl 2-methylpropane-2-sulfinate. The HCl salt was used without further purification. LC-MS (ESI) m/z 218.0 (M+H), RT=1.61 min (Method B).

Workup

  1. customThe solvents were evaporated
  2. additionCH2Cl2 (3×) was added
  3. customevaporated
  4. customdried for 5 h

Sources & evidence

ORD record
ord-5dde90ca36fa4799bb65d4894654b4b7
Source dataset
uspto-grants-2015_02
Patent number
US08946430B2

Reaction notes

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