Propanal → HCID 68816428, compound

HRID 734358Notes

Reaction equation

HRID 734358 reaction equation
[ClH:1].[C:2]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)#[N:3].[CH:24](=O)[CH2:25][CH3:26].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl.O.C(N(CC)CC)C>[ClH:1].[CH2:24]([N:21]1[CH2:20][CH2:19][N:18]([C:16]([CH:13]2[CH2:12][CH2:11][N:10]([C:7]3[CH:6]=[CH:5][C:4]([C:2]#[N:3])=[CH:9][CH:8]=3)[CH2:15][CH2:14]2)=[O:17])[CH2:23][CH2:22]1)[CH2:25][CH3:26]

Participants

8

Reactant 4

HCID 527PropanalHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 68815803HCID 68815803, compound

Product 1

HCID 68816428HCID 68816428, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of 1-[1-(4-cyanophenyl)-piperidine-4-carbonyl]-piperazine hydrochloride (D34) (0.3 g) in dry DCM (10 ml) was treated with triethylamine (0.25 ml) and propionaldehyde (0.25 ml). The reaction mixture was stirred at rt for 30 min. Sodium triacetoxyborohydride (3.7 g) was added and the reaction was stirred at rt overnight. The reaction mixture was treated with 1N NaOH (2 ml) and stirred at rt for 15 min followed by the addition of water (20 ml) and DCM (20 ml). The organic layer was dried (MgSO4) and filtered and the filtrate was absorbed onto silica gel (5 g) and purified by column chromatography (silica gel, step gradient 0-10% MeOH (containing 10% 0.88 ammonia solution) in DCM]. The fractions containing the required product were evaporated and the free base was dissolved in MeOH (1 ml) and treated with ethereal HCl to give the title compound (E116) as a solid (50 mg). MS electrospray; (+ve ion) 341 (MH+).

Workup

  1. stirringthe reaction was stirred at rt overnight
  2. stirringstirred at rt for 15 min
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customthe filtrate was absorbed onto silica gel (5 g)
  6. custompurified by column chromatography (silica gel, step gradient 0-10% MeOH (containing 10% 0.88 ammonia solution) in DCM]
  7. additionThe fractions containing the required product
  8. customwere evaporated
  9. dissolutionthe free base was dissolved in MeOH (1 ml)
  10. additiontreated with ethereal HCl

Sources & evidence

ORD record
ord-d28a3cc3e18b434290c58c8e1acc5e93
Source dataset
uspto-grants-2009_09
Patent number
US07592347B2

Reaction notes

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