Morpholine → 4-(4-Bromo-2-ethyl-benzyl)-morpholine

HRID 1438268Notes

Reaction equation

HRID 1438268 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[C:4]([CH2:10][CH3:11])[CH:3]=1.C(N(CC)CC)C.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CC#N>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[C:4]([CH2:10][CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 587640754-Bromo-1-(bromomethyl)-2-ethylbenzene

Product 1

HCID 587642074-(4-Bromo-2-ethyl-benzyl)-morpholineYield 98.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-bromo-1-bromomethyl-2-ethyl-benzene (3.67 g, 13.2 mmol) in CH3CN (66 mL) was added triethylamine (2.76 mL, 19.8 mmol) and morpholine (1.38 mL, 15.8 mmol). The mixture was stirred for 1.5 hours, at which time the volatiles were removed in vacuo to yield a pale yellow solid (3.7 g, 97%). 1H NMR (300 MHz, CDCl3): δ 1.19 (t, J=7.5 Hz, 3H), 2.40 (m, 4H), 2.68 (q, J=7.7 Hz, 2H), 3.40 (s, 2H), 3.65 (m, 4H), 7.13 (m, 1H), 7.22 (d, J=2.1 Hz, 1H), 7.30 (d, J=2.1 Hz, 1H).

Workup

  1. customwere removed in vacuo

Sources & evidence

ORD record
ord-9539f90262314d5b96e915f2315a1bf3
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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