Hydrochloric Acid → HCID 22712048, compound

HRID 352434

Reaction equation

HRID 352434 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH3:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:16]1([CH:19]=O)[CH2:18][CH2:17]1.C([BH3-])#N.[Na+].Cl>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:19][CH:16]2[CH2:18][CH2:17]2)[CH3:15])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 123114CyclopropanecarboxaldehydeHCID 41361281-benzyl-N-methylpiperidin-4-amineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 22712048HCID 22712048, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

18.9 g of 1-benzyl-4-methylaminopiperidine in the form of the oil prepared in a) are taken up in 250 ml of methanol, combined with 8.3 g of cyclopropane carboxaldehyde and 11.3 g of sodium cyanoborohydride. The mixture is stirred for 5 hours at 40-50° C., then for about 16 hours at ambient temperature. It is then acidified with 2 N hydrochloric acid, evaporated to dryness in vacuo and the residue is taken up in water. It is washed with ether, made alkaline with concentrated sodium hydroxide solution and extracted with ether/ethyl acetate. The organic extract is dried over sodium sulphate and freed from solvents in vacuo. 22.7 g of 1-benzyl-4-(cyclopropylmethyl-methyl-amino)-piperidine are obtained as a yellowish oil.

Workup

  1. waitfor about 16 hours at ambient temperature
  2. customevaporated to dryness in vacuo
  3. washIt is washed with ether
  4. extractionextracted with ether/ethyl acetate
  5. extractionThe organic extract
  6. dry with materialis dried over sodium sulphate

Sources & evidence

ORD record
ord-f8daccd7025a4cf39fdc5c8693be6b22
Source dataset
uspto-grants-2004_06
Patent number
US06747044B2

Linked notes

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