Formaldehyde → 4-(1-Methylpiperidine-2-carbonyl)piperazine-1-carboxylic acid tert-butyl ester

HRID 499228Notes

Reaction equation

HRID 499228 reaction equation
C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:5](C)=O.[Na+].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30]([CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][NH:33]2)=[O:31])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>ClCCCl.C(Cl)Cl>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30]([CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][N:33]2[CH3:5])=[O:31])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 50986447Tert-butyl 4-(piperidine-2-carbonyl)piperazine-1-carboxylate

Product 1

HCID 684576374-(1-Methylpiperidine-2-carbonyl)piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

0.54 ml of 37% aqueous formaldehyde and then 1.41 g of NaBH(OAc)3 are added to a solution of 0.99 g of the compound obtained in step 5.2, in 11 ml of DCE, and the medium is stirred at AT for 12 h. The medium is diluted in DCM and filtered through cotton wool. The organic phase is washed twice with a saturated NaHCO3 solution, and then with a saturated NaCl solution. After drying over MgSO4 and evaporation of the solvents, 0.84 g of the expected product is recovered.

Workup

  1. filtrationfiltered through cotton wool
  2. washThe organic phase is washed twice with a saturated NaHCO3 solution
  3. dry with materialAfter drying over MgSO4 and evaporation of the solvents, 0.84 g of the expected product
  4. customis recovered

Sources & evidence

ORD record
ord-ec7eb7b3d6d14b7b83d53b22e33afc3f
Source dataset
uspto-grants-2010_08
Patent number
US07767681B2

Reaction notes

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