Propanal → 2-Morpholin-4-yl-N,N-dipropyl-1,3-benzothiazol-7-amine

HRID 2235496Notes

Reaction equation

HRID 2235496 reaction equation
[N:1]1([C:7]2[S:8][C:9]3[C:15]([NH2:16])=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH:17](=O)[CH2:18][CH3:19].C(O[BH-](O[C:31](=O)[CH3:32])OC(=O)C)(=O)C.[Na+].Cl[CH:36](Cl)C>C(O)(=O)C>[N:1]1([C:7]2[S:8][C:9]3[C:15]([N:16]([CH2:36][CH2:31][CH3:32])[CH2:17][CH2:18][CH3:19])=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 527PropanalHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 685811022-Morpholin-4-yl-1,3-benzothiazol-7-amine

Product 1

HCID 588965342-Morpholin-4-yl-N,N-dipropyl-1,3-benzothiazol-7-amineYield 30%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Conditions

Temperature
50 °C

Procedure

To 0.022 g (0.094 mmol) of 2-morpholin-4-yl-1,3-benzothiazol-7-amine and 40 μL (0.56 mmol) of propionaldehyde in 2 mL of dichloroethane was added one drop of glacial acetic acid and 0.064 g (0.30 mmol) of sodium triacetoxyborohydride. The mixture was heated to 50° C. for 5 h and concentrated in vacuo. The crude solid was purified by flash chromatography eluting with a 17% ethyl acetate/hexanes mixture to give 0.009 g (30%) of the title compound as a light golden colored oil.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude solid was purified by flash chromatography
  3. washeluting with a 17% ethyl acetate/hexanes mixture

Sources & evidence

ORD record
ord-f439135f697d44b49a6aef889e4ae652
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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