p-Toluenesulfonic acid → 4-(1-Benzylpiperidin-4-yl)morpholine

HRID 1643348Notes

Reaction equation

HRID 1643348 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O.C(O)(=O)C>[C:2]1([CH2:1][N:8]2[CH2:13][CH2:12][CH:11]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 51700761-Benzyl-2-piperidone

Product 1

HCID 7838314-(1-Benzylpiperidin-4-yl)morpholine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

30 mL (0.162 Mol) 1-benzylpiperidone (L) and 16.1 mL (0.185 Mol) morpholine (M) are dissolved in 407 mL tetrahydrofuran at ambient temperature. While cooling, 1.0 g (5 mmol) of p-toluenesulphonic acid and 14.6 mL glacial acetic acid are added, whereupon a jelly-like precipitate is formed. 52.19 g (0.246 Mol) sodium triacetoxyborohydride are added while cooling with ice, during which time the reaction temperature rises to 30° C. After 4 hours at 20° C., 90 mL water are added dropwise. After another 30 minutes, 280 mL of 17% potassium carbonate solution are added. The mixture is stirred intensively, while gas is observed to be given off. After separation of the phases the organic phase is dried and evaporated down.

Workup

  1. temperatureWhile cooling
  2. customis formed
  3. temperaturewhile cooling with ice, during which time the reaction temperature
  4. customrises to 30° C
  5. waitAfter another 30 minutes
  6. customAfter separation of the phases the organic phase
  7. customis dried
  8. customevaporated down

Sources & evidence

ORD record
ord-c083173cdf224952a6c1f78c0760fed0
Source dataset
uspto-grants-2012_02
Patent number
US08119797B2

Reaction notes

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