Methanol → 1-[7-[1-hydroxy-4-(1-piperidyl)butyl]-9H-xanthen-2-yl]-4-(1-piperidyl)butan-1-ol

HRID 436268Notes

Reaction equation

HRID 436268 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][C:10]([C:12]2[CH:25]=[CH:24][C:23]3[O:22][C:21]4[C:16](=[CH:17][C:18]([C:26](=[O:36])[CH2:27][CH2:28][CH2:29][N:30]5[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]5)=[CH:19][CH:20]=4)[CH2:15][C:14]=3[CH:13]=2)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].CO.[OH-].[Na+]>O1CCCC1.O>[N:1]1([CH2:7][CH2:8][CH2:9][CH:10]([C:12]2[CH:25]=[CH:24][C:23]3[O:22][C:21]4[C:16](=[CH:17][C:18]([CH:26]([CH2:27][CH2:28][CH2:29][N:30]5[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]5)[OH:36])=[CH:19][CH:20]=4)[CH2:15][C:14]=3[CH:13]=2)[OH:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 5154014-(1-piperidyl)-1-[7-[4-(1-piperidyl)butanoyl]-9H-xanthen-2-yl]butan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 5154071-[7-[1-hydroxy-4-(1-piperidyl)butyl]-9H-xanthen-2-yl]-4-(1-piperidyl)butan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled, stirred solution of 25.6 g (0.053 moles) of 2,7-bis(4-piperidinobutyryl)xanthene dissolved in 200 ml of tetrahydrofuran is added a solution of 4.2 g (0.11 moles) of sodium borohydride contained in a solution of 50 ml of methanol and 5 ml of a 10% sodium hydroxide solution. The resulting mixture is allowed to warm gradually to room temperature and stirring continued overnight. The reaction mixture is diluted with water and the solid which forms is filtered, washed with water and air dried. The solid product is dissolved in a 10% hydrochloric acid solution, filtered and the filtrate made alkaline with a 10% sodium hydroxide solution. The alkaline filtrate is extracted with methylene chloride. The organic extract is then washed with water, followed by a wash of saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated to dryness in vacuo. The residue containing the desired α,α'-bis(3-piperidinopropyl)xanthene-2,7-dimethanol is recrystallized twice from benzene to yield a product having a m.p. of 145°-6° C.

Workup

  1. filtrationthe solid which forms is filtered
  2. washwashed with water and air
  3. customdried
  4. dissolutionThe solid product is dissolved in a 10% hydrochloric acid solution
  5. filtrationfiltered
  6. extractionThe alkaline filtrate is extracted with methylene chloride
  7. extractionThe organic extract
  8. washis then washed with water
  9. washa wash of saturated sodium chloride solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customevaporated to dryness in vacuo
  13. additionThe residue containing the desired α,α'-bis(3-piperidinopropyl)xanthene-2,7-dimethanol
  14. customis recrystallized twice from benzene
  15. customto yield a product

Sources & evidence

ORD record
ord-87fd3935281f4f698e170fe4b7234c9a
Source dataset
uspto-grants-1977_02
Patent number
US04008240

Reaction notes

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