Sodium Carbonate → HCID 18784693, compound

HRID 1108257Notes

Reaction equation

HRID 1108257 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[O:9][C:10]([CH3:13])=[N:11][N:12]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([N:22]2[C:30]3[CH:29]=[C:28]4[C:31]5([CH2:37][O:38][C:27]4=[CH:26][C:25]=3[CH2:24][CH2:23]2)[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]5)=[O:21])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:46][CH2:47][OH:48]>C(O)C>[OH:48][CH2:47][CH2:46][N:34]1[CH2:33][CH2:32][C:31]2([C:28]3[C:27](=[CH:26][C:25]4[CH2:24][CH2:23][N:22]([C:20]([C:17]5[CH:16]=[CH:15][C:14]([C:3]6[CH:4]=[CH:5][C:6]([C:8]7[O:9][C:10]([CH3:13])=[N:11][N:12]=7)=[CH:7][C:2]=6[CH3:1])=[CH:19][CH:18]=5)=[O:21])[C:30]=4[CH:29]=3)[O:38][CH2:37]2)[CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 108982-BromoethanolHCID 18784688HCID 18784688, compound

Product 1

HCID 18784693HCID 18784693, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 5-(2'-methyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carbonyl)-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (E17 in WO 96/19477, 1.5 g, 2.9 mmole) in ethanol (30 ml) was treated with sodium carbonate (1.2 g, 11.6 mmole) and 2-bromoethanol (0.41 ml, 5.8 mmole) and heated under reflux for 20 hours. The reaction mixture was concentrated in vacuo and the residue treated with water (10 ml) and extracted with chloroform. The extract was dried (Na2SO4), concentrated in vacuo and the residue chromatographed on silica gel eluting with 0-6% methanol/chloroforn to afford the title compound as a yellow solid (0.9 g, 56%). This was converted to its hydrochloride salt and crystallised from acetone m.p. >250° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionthe residue treated with water (10 ml)
  5. extractionextracted with chloroform
  6. dry with materialThe extract was dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customthe residue chromatographed on silica gel eluting with 0-6% methanol/chloroforn

Sources & evidence

ORD record
ord-f888a17933494759aa7f70e406e032bb
Source dataset
uspto-grants-2000_05
Patent number
US06066644

Reaction notes

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