Sodium Carbonate → HCID 43608404, compound

HRID 1785622Notes

Reaction equation

HRID 1785622 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[O:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])([O-])=O.[Na+].[Na+]>ClCCCl.CCOC(C)=O>[CH2:8]([N:5]1[CH2:6][CH2:7][CH:2]([NH:1][CH:18]2[CH2:19][CH2:20][O:15][CH2:16][CH2:17]2)[CH2:3][CH2:4]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 121599Tetrahydro-4H-pyran-4-oneHCID 4158521-Benzyl-4-piperidylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 43608404HCID 43608404, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

19 g of 4-amino-1-benzylpiperidine are placed in 50 ml of 1,2-dichloroethane under dry nitrogen and 10 g of tetrahydropyran-4-one in 20 ml of 1,2-dichloro-ethane are added; after stirring for 10 minutes, 29.6 g of NaBH(OAc)3 are added and the mixture is then stirred for one day. 10% Na2CO3 solution and EtOAc are added to the reaction medium and the phases are then separated by settling. The organic phase is washed with 10% Na2CO3 solution and then with saturated NaCl solution, and then dried over MgSO4 and evaporated under vacuum. 23.4 g of the expected compound are obtained. m.p.=60° C.

Workup

  1. stirringthe mixture is then stirred for one day
  2. customthe phases are then separated
  3. washThe organic phase is washed with 10% Na2CO3 solution
  4. dry with materialwith saturated NaCl solution, and then dried over MgSO4
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-36cabad3c13f4f819dd6cafb2210ee4e
Source dataset
uspto-grants-2009_03
Patent number
US07504511B2

Reaction notes

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