Hydrochloric Acid → HCID 23044277, compound

HRID 2165114Notes

Reaction equation

HRID 2165114 reaction equation
C([BH3-])#N.[Na+].[C:5]1([CH2:11][N:12]2[CH2:17][CH:16]([C:18]([O:20][CH3:21])=[O:19])[C:15](=O)[CH:14]([CH3:23])[CH2:13]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>CO>[C:5]1([CH2:11][N:12]2[CH2:17][CH:16]([C:18]([O:20][CH3:21])=[O:19])[CH:15]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:14]([CH3:23])[CH2:13]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 2724672HCID 2724672, compoundHCID 5003444Sodium cyanoborohydride

Product 1

HCID 23044277HCID 23044277, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium cyanoborohydride (0.69 g, 11 mmole) and 26 g of 30A molecular sieves were slowly added at room temperature to a stirred solution of 1-phenylmethyl-3-methyl-5-methoxycarbonyl-4-piperidone (5.04 g, 18.3 mmole) from Example 3 in 200 ml of methanol, 10.22 g (110 mmole) of aniline and 9.48 ml of 3.86N hydrochloric acid (36.6 mmole) in methanol. The reaction mixture was stirred at room temperature for 3 days, after which time the molecular sieves were filtered off and the solution was made acidic with 10 ml of 20% hydrochloric acid. The methanol was evaporated under vacuum and the residue was diluted with 100 ml of water then extracted with ether. The aqueous layer was then made alkaline with dilute aqueous sodium hydroxide and extracted with 3×100 ml of ether. The combined organic layers were concentrated under vacuum to yield 3.87 g (60%) of crude 1-phenylmethyl-3-methyl-5-methoxycarbonyl-4 -(N-phenylamino)piperidine.

Workup

  1. filtrationafter which time the molecular sieves were filtered off
  2. customThe methanol was evaporated under vacuum
  3. additionthe residue was diluted with 100 ml of water
  4. extractionthen extracted with ether
  5. extractionextracted with 3×100 ml of ether
  6. concentrationThe combined organic layers were concentrated under vacuum

Sources & evidence

ORD record
ord-c39b414e7529458eab98ba7edb3be58b
Source dataset
uspto-grants-1990_07
Patent number
US04939161

Reaction notes

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