Ethanol → HCID 18706915, compound

HRID 1422114Notes

Reaction equation

HRID 1422114 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3=[CH:24][CH:25]=[C:21]4[N:22]3[C:17](=[C:18]([CH2:26][OH:27])[CH:19]=[CH:20]4)[C:16]=2[CH2:28][CH3:29])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl.Cl[CH2:34][CH2:35][N:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1.C(O)C>CS(C)=O.O.C(OCC)C.[Cl-].[Na+].O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:23]3=[CH:24][CH:25]=[C:21]4[N:22]3[C:17](=[C:18]([CH2:26][O:27][CH2:34][CH2:35][N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[CH:19]=[CH:20]4)[C:16]=2[CH2:28][CH3:29])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 18707001HCID 18707001, compound

Product 1

HCID 18706915HCID 18706915, compoundYield 101.3%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-(4-Benzyloxyphenyl)-1-ethyl-7-hydroxymethylpyrrolo[2,1,5-cd]indolizine (0.5 g, 1.3 mmol) was dissolved in 20 ml of dry dimethylsulfoxide under a nitrogen atmosphere. Sodium hydride (100%) (136 mg, 5.7 mmol) was added in portions and stirring was continued for ten minutes. 1-(2-Chloroethyl)pyrrolidine hydrochloride (0.33 g, 1.94 mmol) was added, and the solution was stirred for 4 hours. Ethanol (2 ml) was added dropwise, and the reaction mixture was diluted with 50 ml of water, 50 ml of diethyl ether and 50 ml of brine. The organic material was extracted into diethyl ether (2×50 ml), and the combined organic layers were washed with 3×50 ml of water, 25 ML of brine, dried overmagnesium sulfate, treated with decolourising charcoal and filtered through celite. The solvent was evaporated and the crude product was purified by column chromatography over silica gel 60, using 10% of methanol in dichloromethane as the eluent to afford 0.63 g (100%) of 2-(4-benzyloxyphenyl)-1-ethyl-7-((2-pyrrolidinoethoxy)methyl)pyrrolo[2,1,5-cd]indolizine as a yellow oil. 1H--NMR (CDCl3, 200 MHz) δ: 1.44 (t, 3 H); 1.82 (m, 4 H); 2.70 (m, 4 H); 2.85 (t, 2 H); 3.29 (q, 2 H); 3.82 (t, 2 H); 5.19 (s, 2 H); 5.24 (s, 2 H); 7.11-7.24 (m, 3 H); 7.31-7.60 (m, 6 H); 7.65-7.79 (m, 3 H); 7.89 (d, 1 H).

Workup

  1. waitwas continued for ten minutes
  2. stirringthe solution was stirred for 4 hours
  3. extractionThe organic material was extracted into diethyl ether (2×50 ml)
  4. washthe combined organic layers were washed with 3×50 ml of water, 25 ML of brine
  5. dry with materialdried overmagnesium sulfate
  6. additiontreated with decolourising charcoal
  7. filtrationfiltered through celite
  8. customThe solvent was evaporated
  9. customthe crude product was purified by column chromatography over silica gel 60

Sources & evidence

ORD record
ord-2d4ee9d5a98e4385ac13ad72d4458454
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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