Formaldehyde → HCID 58786454, compound

HRID 1376040Notes

Reaction equation

HRID 1376040 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:15]N)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24]=O.[BH3-][C:27]#[N:28].[Na+]>CC#N.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:15][N:28]([CH3:27])[CH3:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 58786581HCID 58786581, compound

Product 1

HCID 58786454HCID 58786454, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-[2-Amino-1-(4-chloro-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester (203) (0.18 g, 0.529 mmol) in MeCN (3.0 mL) at 0° C. was added formaldehyde(0.64 g, 21.18 mmol) and NaCNBH3 (0.17 g, 2.65 mmol). The reaction was allowed to warm to room temperature over 1 h. The reaction mixture was concnetrated to dryness. The resulting residue was taken up in EtOAc (50 mL) and washed with sat. NaHCO3 (50 mL) and H2O (50 mL). The desired product was then extracted into 1N HCl (50 mL) and washed with EtOAc. This aqueous phase was made alkaline with 5N NaOH (25 mL) and the desired product was extracted into EtOAc (100 mL). The organic phase was concentrated to dryness yielding 0.10 g (53%) product.

Workup

  1. washwashed with sat. NaHCO3 (50 mL) and H2O (50 mL)
  2. extractionThe desired product was then extracted into 1N HCl (50 mL)
  3. washwashed with EtOAc
  4. extractionthe desired product was extracted into EtOAc (100 mL)
  5. concentrationThe organic phase was concentrated to dryness

Sources & evidence

ORD record
ord-996d552fdc764fa1a082d0dccff3d468
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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