2-Pyridinemethanamine → N-(2-tert-butoxybenzyl)-1-(pyridin-2-yl)methanamine

HRID 403115Notes

Reaction equation

HRID 403115 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[C:9]([O:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=O)([CH3:12])([CH3:11])[CH3:10].[BH4-].[Na+]>CC#N>[C:9]([O:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][NH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 195092-PyridinemethanamineHCID 4311764Sodium borohydrideHCID 149555262-tert-Butoxybenzaldehyde

Product 1

HCID 70896659N-(2-tert-butoxybenzyl)-1-(pyridin-2-yl)methanamineYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(Aminomethyl)pyridine (0.849 g, 7.85 mmol) and 8 (1.4 g, 7.8 mmol) were added to 150 mL of CH3CN and the reaction mixture was refluxed under argon for 4 hr. After cooling down to room temperature, the solvent was removed and the residue was redissolved in MeOH. The solvent was then evaporated and NaBH4 (1.485 g, 39 mmol) was added and stirred overnight. The solvent was evaporated, followed by extraction with CH2Cl2. The CH2Cl2 extract was concentrated and purified by a silica gel column using 3% methanolic NH3 (7 M NH3 in methanol/97% CH2Cl2 as eluent to yield the desired product as a pale yellow oil (58%). 1H NMR (CDCl3) δ 8.530 (m, 1H, Ar), 7.604 (ddd, 1H, Ar), 7.330 (m, 2H, Ar), 7.128 (m, 2H, Ar), 7.027 (d, 2H, Ar), 6.969 (ddd, 1H, Ar), 3.892 (s, 2H, —CH2—), 3.837 (s, 2H, —CH2—), 2.523 (s, 1H, —CH—), 1.373 (s, 9H, —C(CH3)3). Mass Spec.=271.18 (M+H)+.

Workup

  1. temperaturethe reaction mixture was refluxed under argon for 4 hr
  2. customthe solvent was removed
  3. dissolutionthe residue was redissolved in MeOH
  4. customThe solvent was then evaporated
  5. customThe solvent was evaporated
  6. extractionfollowed by extraction with CH2Cl2
  7. extractionThe CH2Cl2 extract
  8. concentrationwas concentrated
  9. custompurified by a silica gel column

Sources & evidence

ORD record
ord-ae6fa952ed2347088d06e258a4598a92
Source dataset
uspto-grants-2014_06
Patent number
US08747810B2

Reaction notes

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