Sodium Carbonate → HCID 18784691, compound

HRID 1108258Notes

Reaction equation

HRID 1108258 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+].Cl.[CH3:46][N:47]([CH3:51])[CH2:48][CH2:49]Cl>C(O)C>[CH3:46][N:47]([CH3:51])[CH2:48][CH2:49][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 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 18784688HCID 18784688, compound

Product 1

HCID 18784691HCID 18784691, compoundYield 13.1%

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, 500 mg, 0.99 mmole) in ethanol (40 ml) was treated with sodium carbonate (419 mg, 3.9 mmole) and 2-dimethylaminoethyl chloride hydrochloride (287 mg, 1.98 mmole) and heated under reflux for 48 hours. The reaction mixture was concentrated in vacuo and the residue treated with 10% Na2CO3 solution and extracted with ethyl acetate. The extract was dried (Na2SO4), concentrated in vacuo and the residue chromatographed on silica gel eluting with 0-8% methanol/chloroform to afford the title compound as a yellow/beige solid (75 mg, 13%). This was converted to its hydrochloride salt and crystallised from acetone/ether m.p. 246-248° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 48 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionthe residue treated with 10% Na2CO3 solution
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customthe residue chromatographed on silica gel eluting with 0-8% methanol/chloroform

Sources & evidence

ORD record
ord-9e91fcf62d314b57b4de93cda53866d8
Source dataset
uspto-grants-2000_05
Patent number
US06066644

Reaction notes

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