Formaldehyde → HCID 45275162, compound

HRID 1667190Notes

Reaction equation

HRID 1667190 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[N:9]2[CH2:14][CH2:13][N:12]([C:15](=[O:30])[CH2:16][N:17]3[CH2:22][CH2:21][NH:20][CH:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:18]3=[O:29])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.C=O.[C:40]([BH3-])#N.[Na+]>CO.C(O)(=O)C.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[N:9]2[CH2:10][CH2:11][N:12]([C:15](=[O:30])[CH2:16][N:17]3[CH2:22][CH2:21][N:20]([CH3:40])[CH:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:18]3=[O:29])[CH2:13][CH2:14]2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 45275278HCID 45275278, compound

Product 1

HCID 45275162HCID 45275162, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-{4-[bis(4-fluorophenyl)methyl]piperazin-1-yl}-2-oxoethyl)-3-phenylpiperazin-2-one (Example 103B, 0.1 g, 0.2 mmol) in methanol was added 30% aqueous formaldehyde solution (0.06 mL, 0.3 mmol) and sodium cyanoborohydride (0.02 g, 0.3 mmol). A few drops of acetic acid were added, and the reaction was stirred at ambient temperature overnight. The reaction mixture was diluted with methylene chloride and washed with aqueous bicarbonate solution. The organic layer was separated, dried over MgSO4, evaporated and chromatographed, eluting with 5% methanol/methylene chloride to yield the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.37-7.42 (m, 2H), 7.26-7.35 (m, 7H), 6.94-7.01 (m, 4H), 4.22 (d, J=15.3 Hz, 1H), 4.21 (s, 1H), 4.09 (d, J=15.5 Hz, 1H), 3.79 (s, 1H), 3.73-3.83 (m, 1H), 3.60 (t, J=4.7 Hz, 2H), 3.34-3.43 (m, 3H), 3.03 (ddd, J=12.0, 4.2, 2.9 Hz, 1H), 2.78 (ddd, J=12.0, 10.7, 3.9 Hz, 1H), 2.29-2.37 (m, 4H), 2.20 (s, 3H); MS (ESI+) m/z 519 (M+H)+.

Workup

  1. washwashed with aqueous bicarbonate solution
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customchromatographed
  6. washeluting with 5% methanol/methylene chloride

Sources & evidence

ORD record
ord-693180c98abc48f4ac204def357f07b0
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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