Ethanol → HCID 18707006, compound

HRID 1422083Notes

Reaction equation

HRID 1422083 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[N:11]3[C:15](=[CH:16][CH:17]=1)[C:14]([CH2:18][CH3:19])=[C:13]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:22][CH:21]=1)[C:12]3=[C:34]([CH2:36][O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]Cl)[CH:35]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[NH:46]1[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1.C(O)C>CN(C)C=O.O>[CH2:1]([O:8][C:9]1[C:10]2[N:11]3[C:15](=[CH:16][CH:17]=1)[C:14]([CH2:18][CH3:19])=[C:13]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:22][CH:21]=1)[C:12]3=[C:34]([CH2:36][O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][N:46]1[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1)[CH:35]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8082PiperidineHCID 24758Sodium hydrideHCID 18706962HCID 18706962, compound

Product 1

HCID 18707006HCID 18707006, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-Benzyloxy-2-(4-benzyloxyphenyl)-3-((5-chloropentyloxy)methyl)-1-ethylpyrrolo[2,1,5-cd ]indolizine (0.41 g, 0.69 mmol) was dissolved in 50 ml of dry dimethylformamide under a nitrogen atmosphere. Sodium hydride (60% in oil) (0.40 g, 10 mmol) and piperidine (0.93 g, 11mmol) was added, and the mixture was stirred at 60° for 5 days. Ethanol (10 ml) was added dropwise, and the reaction mixture was diluted with 200 ml of water. The organic material was extracted into ethyl acetate (3×100 ml), and the combined organic layers were washed with brine and dried over sodium sulfate. The solvent was evaporated and the crude produce was purified by column chromatography over silica gel 60, using 10% of methanol in dichloromethane as the eluent. Fractions containing the product were collected and crystallised from diethyl ether and dichloromethane to afford 161 mg (36%) of 5-benzyloxy-2-(4-benzyloxyphenyl)-1-ethyl-3-((5-piperidinopentyloxy)methyl)pyrrolo[2,1,5-cd ]indolizine as yellow crystals. M.p. 106-107° C. MS(SP): m/z 627 (M+1). 1H-NMR (DMSO-d6, 300 MHz) δ: 1.16-1.75 (m, 15H); 2.61-2.95 (m, 4H); 3.07 (q, 2H); 3.21-3.24 (m, 4H); 4.71 (s, 2H); 5.20 (s, 2H); 5.56 (s, 2,H); 7.30-7.64 (m, 14H); 7.99 (d, 1H).

Workup

  1. extractionThe organic material was extracted into ethyl acetate (3×100 ml)
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated
  5. customthe crude produce
  6. customwas purified by column chromatography over silica gel 60
  7. additionFractions containing the product
  8. customwere collected
  9. customcrystallised from diethyl ether and dichloromethane

Sources & evidence

ORD record
ord-2c98f496b4e44e8b9673bed68211b709
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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