Water → Rac-3-cyclohexyl-1-methyl-piperidin-3-ylamine

HRID 2177489Notes

Reaction equation

HRID 2177489 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:13][N:12]([CH3:14])[C:11](=O)[CH2:10][CH2:9]1.O.[OH-].[Na+]>O1CCCC1.COC(C)(C)C>[CH:16]1([C:8]2([NH2:7])[CH2:9][CH2:10][CH2:11][N:12]([CH3:14])[CH2:13]2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59438513HCID 59438513, compound

Product 1

HCID 59438512Rac-3-cyclohexyl-1-methyl-piperidin-3-ylamineYield 87.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
65 °C

Procedure

To 2.06 ml of a 2.5M lithium aluminium hydride solution in tetrahydrofuran cooled to 0° C. was added dropwise a solution of 452 mg (2.15 mmol) rac-5-amino-5-cyclohexyl-1-methyl-piperidin-2-one in 6 ml tetrahydrofuran. Then the solution was heated to 65° C. for 1 hour. The turbid reaction solution was cooled with an ice bath and below 12° C. were added drop-wise 0.13 ml water, 0.32 ml 2N NaOH and further 0.19 ml water. The suspension was diluted with tert-butyl methyl ether, dried over sodium sulfate, filtered and evaporated: 368 mg title compound were obtained as colourless oil which was used without purification for the next step.

Workup

  1. customThe turbid reaction solution
  2. temperaturewas cooled with an ice bath and below 12° C.
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-1d3d82e709a2400bb230bab158d27f93
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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