Hydrochloric Acid → 1-Benzyl-4-(cyclopropylmethyl-methyl-amino)-piperidine

HRID 1167583Notes

Reaction equation

HRID 1167583 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 227120481-Benzyl-4-(cyclopropylmethyl-methyl-amino)-piperidineYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

18.9 g of 1-benzyl-4-methylaminopiperidine as the oil prepared according to a) are taken up in 250 ml of methanol and combined with 8.3 g of cyclopropanecarboxaldehyde and 11.3 g of sodium cyanoborohydride. The mixture is stirred for 5 hours at 40-50° C., then for about another 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 the solvents in vacuo. 22.7 g 1-benzyl-4-(cyclopropylmethyl-methyl-amino)-piperidine are obtained as a yellowish oil.

Workup

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

Sources & evidence

ORD record
ord-c87610091a2a453d88670e64d5042b14
Source dataset
uspto-grants-2003_09
Patent number
US06620438B2

Reaction notes

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