Hydrochloric Acid → 4-(1-Amino-propyl)-4-trifluoromethyl-cyclohexanol

HRID 1948165Notes

Reaction equation

HRID 1948165 reaction equation
C([Si](C)(C)[O:6][CH:7]1[CH2:12][CH2:11][C:10]([CH:17]([NH:20]S(C(C)(C)C)=O)[CH2:18][CH3:19])([C:13]([F:16])([F:15])[F:14])[CH2:9][CH2:8]1)(C)(C)C.Cl.OP([O-])([O-])=O.[K+].[K+]>CC(O)C>[NH2:20][CH:17]([C:10]1([C:13]([F:14])([F:15])[F:16])[CH2:11][CH2:12][CH:7]([OH:6])[CH2:8][CH2:9]1)[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24450Potassium Phosphate, DibasicHCID 67072554HCID 67072554, compound

Product 1

HCID 583808434-(1-Amino-propyl)-4-trifluoromethyl-cyclohexanolYield 91.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3.22 g (7.26 mmol) of 2-Methyl-propane-2-sulfinic acid {1-[4-(tert-butyl-dimethyl-silanyloxy)-1-trifluoromethyl-cyclohexyl]-propyl}-amide (73) were dissolved using 200 ml of 2-propanol. 60 ml of a 10% aqueous solution of HCl was added and the mixture was stirred for 5 h at ambient temperature and the mixture allowed to stand at ambient temperature for 16 h. Afterwards, 300 ml of a saturated aqueous solution of K2HPO4 were added and the 2-propanol evaporated. The resulting mixture was extracted twice using 100 ml of ethyl acetate each. The organic layer was dried using MgSO4 and evaporated to yield 1.50 g of 74 as an oil, used without further purification. Rt=0.82 min (Method P).

Workup

  1. waitto stand at ambient temperature for 16 h
  2. customthe 2-propanol evaporated
  3. extractionThe resulting mixture was extracted twice
  4. customThe organic layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-051112a5f65a4c10bd18922b09a54ea3
Source dataset
uspto-grants-2013_03
Patent number
US08399482B2

Reaction notes

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