Hydroxyamine hydrochloride → HCID 68325445, compound

HRID 571820Notes

Reaction equation

HRID 571820 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 temperature for 16 hours and then at 60° C. for 5 hours. The reaction mixture was then concentrated in vacuo and 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]+).

Workup

  1. waitat 60° C. for 5 hours
  2. concentrationThe reaction mixture was then concentrated 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-aa7775f78e2c4b17ad1a50e9d213360c
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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