HCID 57318325, compound → HCID 19784381, compound

HRID 257086Notes

Reaction equation

HRID 257086 reaction equation
[NH:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:18])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)C(C)=O>[OH-].[Na+].CO>[NH2:1][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:12][CH2:13][CH:14]([N:17]([CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH3:18])[CH2:15][CH2:16]2)=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 57318325HCID 57318325, compound

Product 1

HCID 19784381HCID 19784381, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

5.5 g (16.3 mmol) of the product from Example 7 were refluxed in a mixture of 100 ml of 2M sodium hydroxide solution and 200 ml of methanol for 12 h. The reaction mixture was then concentrated under reduced pressure, the residue was partitioned between water and methylene chloride, and the organic phase was dried and concentrated under reduced pressure. 2.8 g of 1-(4-aminophenyl)-4-(N-benzyl-N-methylamino)piperidine were obtained as an oil which crystallized as difumarate. Melting point 138° C.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customthe residue was partitioned between water and methylene chloride
  3. customthe organic phase was dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-170e9496a2c24b809ded1b7dac4d149a
Source dataset
uspto-grants-1993_11
Patent number
US05260318

Reaction notes

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