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

HRID 2387075Notes

Reaction equation

HRID 2387075 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 Hz, 1 H), 7.30 (d, J=2.1 Hz, 1 H).

Workup

  1. customwere removed in vacuo

Sources & evidence

ORD record
ord-123cfd7bdfa24a2ea46d8b8d89900dbd
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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