Hydroxyamine hydrochloride → 4-[Dimethylamino-(3-fluorophenyl)-methyl]-cyclohexane-carbaldehyde oxime

HRID 557519Notes

Reaction equation

HRID 557519 reaction equation
[CH3:1][N:2]([CH:4]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[CH:5]1[CH2:10][CH2:9][CH:8]([CH:11]=O)[CH2:7][CH2:6]1)[CH3:3].Cl.[NH2:21][OH:22]>C(O)C>[CH3:1][N:2]([CH:4]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[CH:5]1[CH2:10][CH2:9][CH:8]([CH:11]=[N:21][OH:22])[CH2:7][CH2:6]1)[CH3:3]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 866278884-[Dimethylamino-(3-fluorophenyl)-methyl]-cyclohexane-carbaldehyde

Product 1

HCID 743166504-[Dimethylamino-(3-fluorophenyl)-methyl]-cyclohexane-carbaldehyde oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The carbaldehyde 34 (6.32 g, 24 mmol) and hydroxylamine hydrochloride (2.5 g, 36 mmol) were dissolved in abs. ethanol (90 ml); basic ion exchanger Amberlyst A21 (17 g) was added and stirring was carried out for 3.5 h at RT. The ion exchanger was filtered off and washed with ethanol (2×50 ml). The solution was concentrated and the residue was adjusted to pH 11 with 5N NaOH. The aqueous phase was extracted with ethyl acetate (3×50 ml) and the organic phase was dried over sodium sulfate and concentrated in vacuo.

Workup

  1. addition(17 g) was added
  2. filtrationThe ion exchanger was filtered off
  3. washwashed with ethanol (2×50 ml)
  4. concentrationThe solution was concentrated
  5. extractionThe aqueous phase was extracted with ethyl acetate (3×50 ml)
  6. dry with materialthe organic phase was dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-644c1ad4cab948b5a1495c2aa7e9688d
Source dataset
uspto-grants-2011_11
Patent number
US08058475B2

Reaction notes

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