Isopropanol → HCID 20511173, compound

HRID 1164510Notes

Reaction equation

HRID 1164510 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:17]([O:19][CH:20]([O:23][CH2:24][CH3:25])[CH2:21]Br)[CH3:18].C(O)(C)C>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:21][CH:20]([O:23][CH2:24][CH3:25])[O:19][CH2:17][CH3:18])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 24758Sodium hydride2×HCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 20511173HCID 20511173, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1-Benzyl-4-hydroxy piperidine (11.5 g.) dissolved in dry dimethylformamide (DMF) (25 ml.) was added dropwise to a stirred suspension of sodium hydride (2.8 g. of 50% dispersion in oil in dry DMF [25 ml.]), under dry nitrogen, and then stirred at room temperature for 3 hours. The suspension was cooled in an ice/water bath while 2-bromoacetaldehyde diethylacetal (13.0 g.) in dry dimethylformamide (25 ml.) was added dropwise, followed by stirring at room temperature for 24 hours. The above process was repeated to add more sodium hydride (2.8 g.) and the acetal (13.0 g.). Iso-propyl alcohol (50 ml.) was added, and the mixture was stirred for 1/2 hour, followed by filtration through "Hyflo" (Trademark). The filtrate was concentrated in vacuo, suspended in water (100 ml.) and basified to pH 11 with 5 N sodium hydroxide. After extraction with chloroform (2×100 ml.) the combined extracts were taken to dryness in vacuo to give an orange oil which was distilled in vacuo to give 1-benzyl-4-(2,2-diethoxyethoxy)-piperidine (14.1 g.), b.p. 152° [email protected] mm.

Workup

  1. additionwas added dropwise
  2. stirringby stirring at room temperature for 24 hours
  3. stirringthe mixture was stirred for 1/2 hour
  4. filtrationfollowed by filtration through "Hyflo" (Trademark)
  5. concentrationThe filtrate was concentrated in vacuo
  6. extractionAfter extraction with chloroform (2×100 ml.) the combined extracts
  7. customto give an orange oil which
  8. distillationwas distilled in vacuo

Sources & evidence

ORD record
ord-a93d417a30dc416291e2fbe2cd746f87
Source dataset
uspto-grants-1983_01
Patent number
US04370328

Reaction notes

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