Nitrogen → HCID 44213309, compound

HRID 864473Notes

Reaction equation

HRID 864473 reaction equation
[CH2:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][NH:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.Cl[CH2:15][CH2:16][N:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[NH:19][C:18]1=[O:26].C(=O)([O-])[O-].[Na+].[Na+].N#N>C(C(C)=O)C(C)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][N:2]1[CH2:15][CH2:16][N:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[NH:19][C:18]1=[O:26])=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

7

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 107838Tetrahydro-beta-carbolineHCID 36534711-(2-Chloroethyl)-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 44213309HCID 44213309, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole (1.50 g, 8.7 mmol) was suspended in methyl isobutyl ketone (50 ml). 1-(2-Chloroethyl)-1,3-dihydro-2H-benzimidazol-2-one (1.958 g, 9.58 mmol) was added to the mixture along with sodium carbonate (1.110 g, 10.45 mmol) and tetrabutyl ammonium iodide (10 mg). The suspension was heated to 90° C. for 2 days, under an inert (N2) atmosphere. The mixture was concentrated in vacuo to dryness. Water (70 ml) was added, followed by addition of 2N HCl to pH1. The mixture was extracted with CHCl3 (2×70 ml), basified to pH10 using 5N NaOH, and again extracted with CHCl3 (3×70 ml). The organics were combined and washed with brine, separated and dried over MgSO4. The resulting solid was purified by chromatography (CHCl3, MeOH (2%)) to yield a yellow solid, m.p. 214°-216° C.

Workup

  1. concentrationThe mixture was concentrated in vacuo to dryness
  2. additionWater (70 ml) was added
  3. additionfollowed by addition of 2N HCl to pH1
  4. extractionThe mixture was extracted with CHCl3 (2×70 ml)
  5. extractionagain extracted with CHCl3 (3×70 ml)
  6. washwashed with brine
  7. customseparated
  8. dry with materialdried over MgSO4
  9. customThe resulting solid was purified by chromatography (CHCl3, MeOH (2%))
  10. customto yield a yellow solid, m.p. 214°-216° C.

Sources & evidence

ORD record
ord-be6ae52d6c9c43498622d8347194c10c
Source dataset
uspto-grants-1996_10
Patent number
US05563147

Reaction notes

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