Cyclopropanecarbonyl chloride → [9-(2,5-Dichlorobenzyl)-9H-beta-carbolin-3-yl]methyl cyclopropanecarboxylate

HRID 992565Notes

Reaction equation

HRID 992565 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:3]=1[CH2:4][N:5]1[C:17]2[CH:16]=[N:15][C:14]([CH2:18][OH:19])=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2.[CH:25]1([C:28](Cl)=[O:29])[CH2:27][CH2:26]1>C(Cl)Cl.CCOCC>[CH:25]1([C:28]([O:19][CH2:18][C:14]2[N:15]=[CH:16][C:17]3[N:5]([CH2:4][C:3]4[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:2]=4[Cl:1])[C:6]4[C:11]([C:12]=3[CH:13]=2)=[CH:10][CH:9]=[CH:8][CH:7]=4)=[O:29])[CH2:27][CH2:26]1

Participants

5

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 9928662[9-(2,5-Dichlorobenzyl)-9H-beta-carbolin-3-yl]methanol

Product 1

HCID 9888629[9-(2,5-Dichlorobenzyl)-9H-beta-carbolin-3-yl]methyl cyclopropanecarboxylateYield 63.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of [9-(2,5-dichlorobenzyl)-9H-β-carbolin-3-yl]methanol (357 mg, 1.0 mmol) and cyclopropyl carbonyl chloride (133 mg, 1.27 mmol) in methylene chloride (5 mL) was allowed to stand for 10 minutes. The solvent was evaporated, and the residue partitioned between aqueous Na2CO3 and methylene chloride. The extract was dried over Na2SO4, filtered and evaporated, affording a resin. This was dissolved in ether and filtered through a plug of silica gel, treated with ethereal hydrogen chloride, evaporated, and the residue recrystallized from ethanol/ethyl acetate/ether, affording 270 mg (58%) of the title compound as a yellow solid. 1H NMR (CDCl3) δ8.85 (s, 1H), 8.44 (s, 1 H), 8.25 (d, J=7.9 Hz, 1H), 7.58 (t, J=7.5 Hz, 1H), 7.35-7.28 (m, 3H), 7.10 (dd, J=8, 2.3 Hz, 1H), 6.37 (d, J=2.3 Hz, 1H), 5.62 (s, 2H), 5.46 (s, 2H), 1.74 (m, 2H), 1.56 (m, 1H), 0.84-0.71 (m, 4H); MS (APCI; (M+H)+) m/z 425.

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between aqueous Na2CO3 and methylene chloride
  3. dry with materialThe extract was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customaffording a resin
  7. filtrationfiltered through a plug of silica gel
  8. additiontreated with ethereal hydrogen chloride
  9. customevaporated
  10. customthe residue recrystallized from ethanol/ethyl acetate/ether

Sources & evidence

ORD record
ord-4fbd52b7aa104e8c92ab80bfb5e682a5
Source dataset
uspto-grants-2002_10
Patent number
US06469021B1

Reaction notes

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