Pyrrolidine → HCID 58764212, compound

HRID 859694Notes

Reaction equation

HRID 859694 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.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:4]([CH2:10][CH3:11])[CH:3]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 587640754-Bromo-1-(bromomethyl)-2-ethylbenzene

Product 1

HCID 58764212HCID 58764212, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-1-bromomethyl-2-ethyl-benzene (2.00 g, 7.19 mmol) in CH2Cl2 (30 mL) was added dropwise pyrrolidine (1.19 mL, 14.4 mmol). The mixture was stirred for 15 hours, and then partitioned between Et2O and H2O. The organic layer was washed with brine, dried over MgSO4, and concentrated to yield a yellow oil (1.3 g, 68%). 1H NMR (300 MHz, CDCl3): δ 1.19 (t, J=7.5 Hz, 3 H), 1.76 (m, 4 H), 2.47 (m, 4 H), 2.69 (q, J=7.5 Hz, 2 H), 3.54 (s, 2 H), 7.19 (m, 1 H), 7.25 (m, 1 H), 7.29 (d, J=1.9 Hz, 1 H).

Workup

  1. custompartitioned between Et2O and H2O
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5d37ab67a9314ff3907e7a57e4c2ca90
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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