Triethylamine → HCID 68291108, compound

HRID 2205915Notes

Reaction equation

HRID 2205915 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([O:24][CH3:25])[CH:16]=1>C1COCC1>[CH3:25][O:24][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[N+:21]([O-:23])=[O:22])[CH2:14][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 126216043-Methoxy-4-nitrobenzyl bromide

Product 1

HCID 68291108HCID 68291108, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyrrolidine (0.2 g, 2.8 mmol) and triethylamine (0.28 g, 2.8 mmol) were added to a solution of 4-(bromomethyl)-2-methoxy-1-nitrobenzene (Preparation 104, 0.22 g, 0.894 mmol) in THF (5 mL). The reaction mixture was stirred for 1 hour at room temperature before being concentrated under reduced pressure and purified by silica gel column chromatography eluting with 10% methanol in ethyl acetate to afford the title compound as a pale yellow powder (0.18 g, 94%). 1H-NMR (500 MHz, CDCl3): δ 1.8 (t, J=6.7 Hz, 4H), 2.51 (t, J=6.7 Hz, 4H), 3.65 (s, 2H), 3.96 (s, 3H), 6.96 (dd, J=9.7 Hz, 1.5 Hz 1H), 7.12 (s, 1H), 7.8 (d, J=8.3 Hz, 1H)

Workup

  1. concentrationbefore being concentrated under reduced pressure
  2. custompurified by silica gel column chromatography
  3. washeluting with 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-8ea166a3cfa84b5889be16cfdb7642ee
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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