Ethyl Acetate → Tert-butyl 2-(4-amino-3-bromophenyl)morpholine-4-carboxylate

HRID 571825Notes

Reaction equation

HRID 571825 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Br:28])C(=O)C1.CCOC(C)=O>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][C:3]=1[Br:28]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 58315596tert-Butyl 2-(4-aminophenyl)morpholine-4-carboxylate

Product 1

HCID 71743185Tert-butyl 2-(4-amino-3-bromophenyl)morpholine-4-carboxylateYield 101.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of tert-butyl (RS)-2-(4-aminophenyl)morpholine-4-carboxylate (3.07 g, CAS-1002726-96-6) in DMF (30 ml) was added NBS (1.96 g) and the mixture was stirred at room temperature for 15 min. The reaction mixture was then poured into EtOAc and extracted sequentially with water and with saturated brine. The organic layer was dried over Na2SO4 and then concentrated in vacuo to afford tert-butyl (RS)-2-(4-amino-3-bromophenyl)morpholine-4-carboxylate (4.0 g, quant.) as a light brown solid which was used in the next step without further purification. MS (ISP): 359.0 ([{81Br}M+H]+), 357.0 ([{79Br}M+H]+), 303.0 ([{81Br}M+H—C4H8]+), 301.0 ([{79Br}M+H—C4H8]+).

Workup

  1. extractionextracted sequentially with water and with saturated brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d1e57c5c3354146bac731a9303dac9d
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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