Hydroxyamine hydrochloride → HCID 68325445, compound

HRID 2403318Notes

Reaction equation

HRID 2403318 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]2[O:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23]2)[CH:5]=[CH:6][C:7]=1[N:8]=C(C1C=CC=CC=1)C1C=CC=CC=1.C([O-])(=O)C.[Na+].Cl.NO>CO>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([CH:22]2[O:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[CH2:23]2)=[CH:3][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86671406HCID 86671406, compound

Product 1

HCID 68325445HCID 68325445, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of tert-butyl (RS)-2-(3-chloro-4-(diphenylmethyleneamino)phenyl)morpholine-4-carboxylate (0.63 g) in methanol (8 ml) were added sodium acetate (325 mg) and hydroxylamine hydrochloride (202 mg). The reaction mixture was stirred at room tempearture for 16 hours and then at 60° C. for 1 hour. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 70% EtOAc in hexanes) to afford tert-butyl (RS)-2-(4-amino-3-chlorophenyl)morpholine-4-carboxylate (345 mg, 84%) as a white solid. MS (ISP): 337.2 ([{37Cl}M+Na]+), 335.1 ([{35Cl}M+Na]+), 314.9 ([{37Cl}M+H]+), 313.0 ([{35Cl}M+H]+), 259.1 ([{37Cl}M+H—C4H8]+), 257.1 ([{35Cl}M+H—C4H8]+), 215.3 ([{37Cl}M+H—C4H8—CO2]+), 213.0 ([{35Cl}M+H—C4H8—CO2]+).

Workup

  1. waitat 60° C. for 1 hour
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash column chromatography (silica gel; gradient: 0% to 70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a8541b5f16344e2fb5ba0a11cec02f6d
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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