Formaldehyde → HCID 17946062, compound

HRID 1167064Notes

Reaction equation

HRID 1167064 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:26](C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[N:8]([CH3:26])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 12288800HCID 12288800, compound

Product 1

HCID 17946062HCID 17946062, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of N-[di(2-pyridinyl)methyl]-N-(2-pyridinylmethyl)amine (1.262 g, 4.59 mmol) in 1,2-dichloroethane (35 ml) was added formaldehyde (37% solution in water, 0.45 ml, 6.0 mmol). NaBH(OAc)3 (3.92 g, 18.5 mmol) was added in small portions. After stirring for 7 h at room temperature saturated NaHCO3(aq) (35 ml) was added and the 1,2-dichloroethane layer was separated. The aqueous layer is extracted with CH2Cl2 (3×20 ml). The combined organic layers were washed with 1N NaOH (20 ml) and brine (20 ml), dried (Na2SO4) and the solvent removed in vacuo to give N-[di(2-pyridinyl)methyl]-N-methyl-N-(2-pyridinylmethyl)amine (1.235 g, 4.27 mmol, 93%) as a slightly yellow oil. 1H NMR (CDCl3, 300 MHz) δ 2.19 (s, 3H), 3.72 (s, 2H), 4.96 (s, 1H), 7.14 (m, 3H), 7.71 (m, 6H), 8.56 (m, 3H); 13C NMR (CDCl3, 50 MHz) δ 40.32 (q), 61.04 (t), 77.87 (d), 121.76 (d), 122.10 (d), 122.92 (d), 123.21 (d), 136.29 (d), 136.43 (d), 148.86 (d), 149.22 (d), 159.37 (s), 160.59 (s), MS (CI): m/z 291 (M+1).

Workup

  1. additionwas added
  2. customthe 1,2-dichloroethane layer was separated
  3. extractionThe aqueous layer is extracted with CH2Cl2 (3×20 ml)
  4. washThe combined organic layers were washed with 1N NaOH (20 ml) and brine (20 ml)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-aa1b2ffe74784b5598d68b72f00db547
Source dataset
uspto-grants-2003_09
Patent number
US06617299B1

Reaction notes

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