Hydroxyamine hydrochloride → HCID 74032837, compound

HRID 1955180Notes

Reaction equation

HRID 1955180 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=2)[CH:20]=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:26][OH:27].C([O-])(=O)C.[Na+]>CCO>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=2)[CH:20]=[N:26][OH:27])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 23294407HCID 23294407, compound

Product 1

HCID 74032837HCID 74032837, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 3-((2-(4-benzylpiperidin-1-yl)ethyl)oxy)benzaldehyde (200 mg, 0.620 mmol) in 6 mL of 50% aqueous EtOH was added a solution of hydroxylamine hydrochloride (110 mg, 1.55 mmol) and sodium acetate (246 mg, 2.77 mmol) in 50% aqueous EtOH (10 mL). The resulting solution was allowed to stir at room temperature for 3 days. The EtOH was evaporated and a colorless solid was collected by filtration and dried to give the product (160 mg, 70%): mp 141-143° C.; 1H NMR (CDCl3) 1.40 (m, 2 H), 1.50 (m, 1 H), 1.64 (m, 2 H), 2.12 (m, 2 H), 2.54 (m, 2 H), 2.85 (s, 2 H), 3.08 (m, 2 H), 4.21 (m, 2 H), 6.88-7.28 (m, 9 H), 8.04 (s, 1 H), 10.00 (bs, 1 H).

Workup

  1. customThe EtOH was evaporated
  2. filtrationa colorless solid was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-12e0f08eb45e4255948539a4a35953ff
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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