Tetrahydrofuran → HCID 11436230, compound

HRID 1030898Notes

Reaction equation

HRID 1030898 reaction equation
O1CCCC1.[AlH4-].[Li+].[C:8]1([CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][C:23](OCC)=[O:24])[CH2:17][CH2:16]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+]>O>[C:8]1([CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][CH2:23][OH:24])[CH2:17][CH2:16]2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 28112Lithium aluminum hydrideHCID 14989194Ethyl 3-(1-benzylpiperidin-4-yl)propanoate

Product 1

HCID 11436230HCID 11436230, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

270 Parts of tetrahydrofuran were added carefully to 10 parts of lithium tetrahydroaluminate. A solution of 66 parts of ethyl 1-(phenylmethyl)-4-piperidinepropanoate in 180 parts of tetrahydrofuran was added dropwise to the thus obtained mixture (exothermic reaction, the temperature rose to about 45° C.). The whole was stirred overnight at reflux temperature. The mixture was cooled in an ice salt bath and decomposed at 0° C. with successively 10.5 parts of water, 7.8 parts of a sodium hydroxide solution 20% and 33.8 parts of water. The mixture was filtered over diatomaceous earth and the filtrate was evaporated, yielding 56 parts (100% of 1-(phenylmethyl)-4-piperidinepropanol as a residue (int. 40).

Workup

  1. customexothermic reaction
  2. customrose to about 45° C.
  3. temperatureat reflux temperature
  4. temperatureThe mixture was cooled in an ice salt bath
  5. filtrationThe mixture was filtered over diatomaceous earth
  6. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-86651fae946144908dd87bfeff8e516c
Source dataset
uspto-grants-1992_04
Patent number
US05106973

Reaction notes

Loading…