HCID 59713390, compound → HCID 59713386, compound

HRID 1091240Notes

Reaction equation

HRID 1091240 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:11]2([N+:17]([O-])=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[OH:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1>CO.Cl.[Zn]>[NH2:17][C:11]1([CH:9]([C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)[OH:10])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 1

HCID 59713390HCID 59713390, compound

Product 1

HCID 59713386HCID 59713386, compoundYield 82.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a stirred solution of (3,5-dichloro-phenyl)-(1-nitro-cyclohexyl)-methanol (5.87 g, 19.3 mmol) in methanol (40 mL) and concentrated HCl (10 mL), cooled to ˜5° C., was added zinc powder. The mixture was stirred at room temperature overnight and filtered through Celite. The filter cake was washed with methanol (2×100 mL) and the filtrate was evaporated to dryness. The residue was treated with 5% aqueous NaOH (100 mL) and extracted with ethyl acetate (2×200 mL). The combined organic extracts were dried over Na2SO4 and evaporated to leave (1-amino-cyclohexyl)-(3,5-dichloro-phenyl)-methanol (4.36 g) as a white solid. 1H NMR (500 MHz, CDCl3) δ (ppm): 7.25 (s, 1H), 7.185 (s, 2H), 4.21 (s, 1H), 1.55 (m, 4H), 1.3 (m, 3H), 1.1 (m, 3H).

Workup

  1. filtrationfiltered through Celite
  2. washThe filter cake was washed with methanol (2×100 mL)
  3. customthe filtrate was evaporated to dryness
  4. additionThe residue was treated with 5% aqueous NaOH (100 mL)
  5. extractionextracted with ethyl acetate (2×200 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-d317d83d4d3e45079ba7bb9e3ad8776c
Source dataset
uspto-grants-2012_03
Patent number
US08129355B2

Reaction notes

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