Sodium cyanoborohydride → 2-(2-Pyrrolidin-1-yl-ethyl)-benzooxazol-6-ylamine

HRID 219649Notes

Reaction equation

HRID 219649 reaction equation
[N:1]1([CH:6]=[CH:7][C:8]2[O:9][C:10]3[CH:16]=[C:15]([NH2:17])[CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([BH3-])#N.[Na+]>CO>[N:1]1([CH2:6][CH2:7][C:8]2[O:9][C:10]3[CH:16]=[C:15]([NH2:17])[CH:14]=[CH:13][C:11]=3[N:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 866232152-(2-Pyrrolidin-1-yl-vinyl)-benzooxazol-6-ylamine

Product 1

HCID 691228932-(2-Pyrrolidin-1-yl-ethyl)-benzooxazol-6-ylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(2-pyrrolidin-1-yl-vinyl)-benzooxazol-6-ylamine (3.2 mmol) in MeOH (40 mL) is added sodium cyanoborohydride (6.4 mmol) at room temperature. The reaction mixture is heated to reflux for 18 hours. The mixture is concentrated and the residue is dissolved in DCM. The solution is washed with water and brine, and dried (MgSO4). A small amount of activated carbon is added to the solution, and the mixture is filtered. The filtrate is concentrated to afford 2-(2-pyrrolidin-1-yl-ethyl)-benzooxazol-6-ylamine as a solid. 1H NMR (300 MHz, CDCl3): δ 1.79 (m, 4H), 2.61 (m, 4H), 3.00-3.18 (m, 4H), 4.78 (broad, 2N—H), 6.68 (q, H), 6.80 (d, H), 7.43 (d, H).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 18 hours
  3. concentrationThe mixture is concentrated
  4. dissolutionthe residue is dissolved in DCM
  5. washThe solution is washed with water and brine
  6. dry with materialdried (MgSO4)
  7. additionA small amount of activated carbon is added to the solution
  8. filtrationthe mixture is filtered
  9. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-f90cbe20e5694c918368c4b052befd9c
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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