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

HRID 859684Notes

Reaction equation

HRID 859684 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, 3 H), 2.40 (m, 4 H), 2.68 (q, J=7.7 Hz, 2 H), 3.40 (s, 2 H), 3.65 (m, 4 H), 7.13 (m, 1 H), 7.22 (d, J=2.1 H, 1 H), 7.30 (d, J=2.1 Hz, 1 H).

Workup

  1. customwere removed in vacuo

Sources & evidence

ORD record
ord-0989b403e61348848ebde50e05a37405
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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