Hydroxyamine hydrochloride → HCID 178510845, compound

HRID 470627

Reaction equation

HRID 470627 reaction equation
[Na].Cl.[NH2:3][OH:4].[CH2:5]([N:12]1[CH2:17][CH2:16][CH:15]([CH2:18][C:19]#[N:20])[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CO>[CH2:5]([N:12]1[CH2:17][CH2:16][CH:15]([CH2:18][C:19]([NH:3][OH:4])=[NH:20])[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 5624991-Benzylpiperidine-4-acetonitrile2×HCID 5360545Sodium

Product 1

HCID 178510845HCID 178510845, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
75 °C

Procedure

Sodium metal (0.8 g, 34.78 mmol) was dissolved in dry methanol (10 mL) at 0-10° C. and this solution was added slowly into a suspension of hydroxylamine hydrochloride (2.43 g, 34.96 mmol) in methanol (10 mL) at room temperature. The reaction mixture was stirred for 10 min until a clear solution was obtained, 2-(1-Benzylpiperidin-4-yl)acetonitrile (compound of Example 27; 3 g, 13.99 mmol) in dry methanol (20 mL) was added into the resulting reaction mixture and heated at 75° C. for 13 h. The solvent was evaporated at 50° C. to 55° C. and the crude product obtained was purified by column chromatography (silica gel, chloroform-methanol) to afford the title compound.

Workup

  1. customwas obtained
  2. customThe solvent was evaporated at 50° C. to 55° C.
  3. customthe crude product obtained
  4. customwas purified by column chromatography (silica gel, chloroform-methanol)

Sources & evidence

ORD record
ord-798425f4702045289f068de3a3155a8c
Source dataset
uspto-grants-2014_01
Patent number
US08629277B2

Linked notes

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