Tetrahydrofuran → HCID 15096866, compound

HRID 846796Notes

Reaction equation

HRID 846796 reaction equation
[C:1]1([CH2:7][O:8][C@H:9]2[C@@H:14]([NH:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.[OH-].[Na+].[C:31](Cl)(=[O:35])[O:32][CH2:33][CH3:34]>ClCCl>[C:16]([NH:15][C@H:14]1[CH2:13][CH2:12][N:11]([C:31]([O:32][CH2:33][CH3:34])=[O:35])[CH2:10][C@H:9]1[O:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 67914534HCID 67914534, compound

Product 1

HCID 15096866HCID 15096866, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 40 parts of cis-N-[3-(phenylmethoxy)-4-piperidinyl]benzamide in 153 parts of tetrahydrofuran were added 323 parts of a sodium hydroxide solution 1N. Then there was added dropwise a solution of 15.4 parts of ethyl carbonochloridate in 58 parts of tetrahydrofuran at a temperature below 5° C. Upon completion, stirring was continued for 3 hours while cooling in an ice-bath (temp. below 5° C.). Dichloromethane was added and the layers were separated. The aqueous phase was extracted with dichloromethane. The combined organic phases were washed with water, dried, filtered and evaporated. The residue was suspended in 2,2'-oxybispropane. The product was filtered off and crystallized from acetonitrile. A first fraction was filtered off, yielding 30.2 parts of cis-ethyl 4-(benzoylamino)-3-(phenylmethoxy)-1-piperidinecarboxylate; mp. 139.2° C. The mother liquor was concentrated. The precipitated product was filtered off, yielding a second fraction of 5 parts of cis-ethyl 4-(benzoylamino)-3-(phenylmethoxy)-1-piperidinecarboxylate.

Workup

  1. temperaturewhile cooling in an ice-bath (temp. below 5° C.)
  2. customthe layers were separated
  3. extractionThe aqueous phase was extracted with dichloromethane
  4. washThe combined organic phases were washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. filtrationThe product was filtered off
  9. customcrystallized from acetonitrile
  10. filtrationA first fraction was filtered off

Sources & evidence

ORD record
ord-1bb00d88159348d7a058a91ec36b17b9
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

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