3-Bromoaniline → 4-(3-Bromophenyl)morpholine

HRID 2202651Notes

Reaction equation

HRID 2202651 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Br[CH2:10][CH2:11][O:12][CH2:13][CH2:14]Br.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:5]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 115623-BromoanilineHCID 21521Bis(2-bromoethyl) etherHCID 81531Diisopropylethylamine

Product 1

HCID 49612684-(3-Bromophenyl)morpholineYield 16.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-bromoaniline (1.00 g, 5.81 mmol) in anhydrous DMF (20 mL) was added 1-bromo-2-(2-bromoethoxy)ethane (1.62 g, 6.18 mmol) and DIPEA (2.25 g, 17.4 mmol). The solution was heated to 100° C. for 16 h, cooled and concentrated. The residue was purified by preparative HPLC purification. (230 mg, yield 16.4%) MS (ESI+) e/z: 242.0 [M+1]+.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe residue was purified by preparative HPLC purification

Sources & evidence

ORD record
ord-fa737d0aae944018a065f2f4208db08b
Source dataset
uspto-grants-2016_06
Patent number
US09365555B2

Reaction notes

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