2-Chloroethanol → HCID 9959249, compound

HRID 1108256Notes

Reaction equation

HRID 1108256 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[C:11]([CH3:13])[O:10][N:9]=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-].[K+].[K+].Cl[CH2:46][CH2:47][OH:48]>CC(=O)CC>[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[N:12]=[C:11]([CH3:13])[O:10][N:9]=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 342-Chloroethanol2×HCID 11430Potassium Carbonate2×HCID 18784692HCID 18784692, compound

Product 1

HCID 9959249HCID 9959249, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A stirred solution of 5-(2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl4-carbonyl)-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (E3 in WO 96/19477, 0.44 g, 0.87 mmole) in 2-butanone (30 ml) was treated with potassium carbonate (0.36 g, 2.6 mmole) and 2-chloroethanol (0.18 ml, 2.6 mmole) and heated under reflux for 56 hours, then additional potassium carbonate (0.36 g, 2.6 mmole) and 2-chloroethanol (0.18 ml, 2.6 mmole) added. Reflux was continued for a further 30 hours, then the mixture was concentrated in vacuo and the residue treated with 10% Na2CO3 solution and extracted with ethyl acetate. The extract was dried, concentrated in vacuo and the residue chromatographed on silica gel eluting with 0-10% methanol/chloroforn to afford the title compound as a pale yellow oil (0.18 g, 38%). This was converted to its hydrochloride salt and crystallised from acetone mp. >230° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 56 hours
  3. temperatureReflux
  4. concentrationthe mixture was concentrated in vacuo
  5. additionthe residue treated with 10% Na2CO3 solution
  6. extractionextracted with ethyl acetate
  7. customThe extract was dried
  8. concentrationconcentrated in vacuo
  9. customthe residue chromatographed on silica gel eluting with 0-10% methanol/chloroforn

Sources & evidence

ORD record
ord-a92c4fbf640c45b0bf6c13d2a0197751
Source dataset
uspto-grants-2000_05
Patent number
US06066644

Reaction notes

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