1-Bromo-3-chloropropane → HCID 18940714, compound

HRID 355826Notes

Reaction equation

HRID 355826 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[N:8]=[CH:9][C:10]3[NH:11][C:12]4[C:17]([C:18]=3[CH:19]=2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[O:4][N:3]=1.[H-].[Na+].Br[CH2:23][CH2:24][CH2:25][Cl:26]>CN(C=O)C>[Cl:26][CH2:25][CH2:24][CH2:23][N:11]1[C:10]2[CH:9]=[N:8][C:7]([C:5]3[O:4][N:3]=[C:2]([CH3:1])[N:6]=3)=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 18940704HCID 18940704, compound

Product 1

HCID 18940714HCID 18940714, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-(3-methyl-1,2,4-oxadiazol-5-yl)-β-carboline (2.00 g, 0.008 mol) in anhydrous DMF (50 mL) was added 50% sodium hydride in mineral oil (0.42 g, 0.01 mol). The mixture was stirred for 1 h at room temperature, and then carefully added to a solution of 1-bromo-3-chloropropane (1.39 g, 0.0088 mol) in anhydrous DMF (150 mL). The resulting mixture was stirred at ambient temperature over night. The reaction mixture was concentrated in vacuo, and the crude product was purified on a silica gel column (Eluent: CH2Cl2 /methanol (9:1)) to give the title compound 2.11 g (81%). M.p. 180°-185° C.

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature over night
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe crude product was purified on a silica gel column (Eluent: CH2Cl2 /methanol (9:1))

Sources & evidence

ORD record
ord-02e8817e1089477292efb5574f6cb9b3
Source dataset
uspto-grants-1998_11
Patent number
US05834482

Reaction notes

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