Sodium Iodide → HCID 18465425, compound

HRID 2230173Notes

Reaction equation

HRID 2230173 reaction equation
[C:1]1([C:7]2([N:14]3[CH2:19][CH2:18][CH:17]([N:20]4[C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=5[NH:22][C:21]4=[O:29])[CH2:16][CH2:15]3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC([O-])(C)C.[K+].[C:36]([O:40][C:41]([NH:43][CH2:44][CH2:45]Br)=[O:42])([CH3:39])([CH3:38])[CH3:37].[Na+].[I-]>CN(C=O)C.C1COCC1>[O:29]=[C:21]1[N:22]([CH2:45][CH2:44][NH:43][C:41](=[O:42])[O:40][C:36]([CH3:39])([CH3:38])[CH3:37])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N:20]1[CH:17]1[CH2:18][CH2:19][N:14]([C:7]2([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:15][CH2:16]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 9821733HCID 9821733, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18465425HCID 18465425, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred mixture of 1-[1-(1-phenylcycloheptyl)-4-piperidyl]-1,3-dihydro-2H-1,3-benzimidazol-2-one (100 mg, 0.257 mmol, this was prepared as Example 17) and THF (2 ml) was added t-BuOK (35 mg, 0.308 mmol) at 0° C. Then N-(t-butoxycarbonyl)-2-bromoethylamine (86 mg. 0.385 mmol, this was reported by E. Vedejs et al. J. Org. Chem. 1988, 33, 2226-2232). NaI (8 mg, 0.0513 mmol), and DMF (0.5 ml) were added to the reaction mixture. After 8 h stirring at 60° C., the reaction mixture was concentrated in vacuo. The residue was diluted with CH2Cl2. washed with water, dried (Na2SO4). and filtered. The filtrate was concentrated and the residue was purified by preparative TLC (MeOH/CH2Cl2: 1/10) to give 98 mg (71.6%) of amorphous solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with CH2Cl2
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationand filtered
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by preparative TLC (MeOH/CH2Cl2: 1/10)

Sources & evidence

ORD record
ord-631acd5e453f4e79848aa1df2bf9fd6e
Source dataset
uspto-grants-2002_07
Patent number
US06423725B1

Reaction notes

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