Formaldehyde → HCID 21935152, compound

HRID 1592734Notes

Reaction equation

HRID 1592734 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20]N)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:22]=O.[C:24]([BH3-])#[N:25].[Na+]>CC#N>[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][N:25]([CH3:24])[CH3:22])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 4961274Tert-butyl 4-[2-(aminomethyl)phenyl]piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 21935152HCID 21935152, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

1-Boc-4-(2-aminomethyl-phenyl)-piperazine (2.0 g, 6.86 mmol) was dissolved in CH3CN (15 mL) and cooled to about 0° C. Aqueous formaldehyde (37% wt. in H2O) (7.56 mL) was added to the cold solution followed by the addition of sodium cyanoborohydride (2.15 g, 34.32 mmol). The reaction mixture was allowed to stir at 0° C. for about 5 minutes and then allowed to naturally warm to room temperature. The mixture was then concentrated to dryness. The resulting residue was taken up in EtOAc (100 mL) and washed with saturated NaHCO3 solution (100 mL) and brine (100 mL). The organic phase was concentrated to dryness to afford about 2.2 g of crude material. MS (ESI+) 320.2 [M+1]

Workup

  1. temperatureto naturally warm to room temperature
  2. concentrationThe mixture was then concentrated to dryness
  3. washwashed with saturated NaHCO3 solution (100 mL) and brine (100 mL)
  4. concentrationThe organic phase was concentrated to dryness

Sources & evidence

ORD record
ord-339e49da33f947c29ce4e062927409bc
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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