Water → HCID 58772515, compound

HRID 1361509Notes

Reaction equation

HRID 1361509 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH:10]=[C:11]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 58772035HCID 58772035, compound

Product 1

HCID 58772515HCID 58772515, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-benzyl-4-(5-chloro-2-methoxy-phenyl)-piperidin-4-ol 1b (1.2, 17 g, 0.05 mol) and p-TsOH (29.3 g, 0.15 mol) in toluene (300 mL) was heated to reflux for 6 h with water being removed through a Dean-Stark apparatus. The mixture was cooled to room temperature and was washed with saturated NaHCO3 (100 mL×3). The organic layer was dried over Na2SO4 and concentrated to afford 1-benzyl-4-(5-chloro-2-methoxy-phenyl)-1,2,3,6-tetrahydro-pyridine 1c as a brown liquid.

Workup

  1. customremoved through a Dean-Stark apparatus
  2. washwas washed with saturated NaHCO3 (100 mL×3)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2fdb5124fc9b4d4f94bcaea323c017ca
Source dataset
uspto-grants-2011_02
Patent number
US07880007B2

Reaction notes

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