Acetonitrile → HCID 22256488, compound

HRID 351176Notes

Reaction equation

HRID 351176 reaction equation
C(O[C:6]([N:8]([CH2:28][C:29]1[CH:34]=CC=CN=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][CH:18]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3CCC2)=[CH:12][CH:11]=1)=O)(C)(C)C.BrCC(O[C:40]([CH3:43])([CH3:42])[CH3:41])=O.[C:44](=[O:47])([O-])[O-:45].[K+].[K+].[CH3:50][C:51]#[N:52]>>[N:26]1[CH:25]=[CH:24][CH:23]=[CH:22][C:27]=1[CH2:18][NH:17][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:8]([CH2:6][C:44]([OH:45])=[O:47])[CH:28]2[C:42]3[N:52]=[CH:51][CH:50]=[CH:41][C:40]=3[CH2:43][CH2:34][CH2:29]2)=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 22018600N-(t-butoxycarbonyl)-N-(2-pyridinylmethyl)-N'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

Product 1

HCID 22256488HCID 22256488, compoundYield 56%

Procedure

To a solution of N-(t-butoxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (230 mg, 0.50 mmol) and t-butyl bromoacetate (0.15 mL, 1.02 mmol) in CH3CN (8 mL) was added powdered potassium carbonate (220 mg, 1.60 mmol) and the mixture was stirred for 16 hours. The crude material was purified by column chromatography on silica gel (CH2Cl2/MeOH, 98:2 to 95:5) to give the desired product (160 mg, 56%) as a yellow oil.

Workup

  1. customThe crude material was purified by column chromatography on silica gel (CH2Cl2/MeOH, 98:2 to 95:5)

Sources & evidence

ORD record
ord-8b826863e0fd4b2bbee5acfea9a3ba50
Source dataset
uspto-grants-2007_02
Patent number
US07183273B2

Reaction notes

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