Isopropylamine → HCID 178457182, compound

HRID 1054532Notes

Reaction equation

HRID 1054532 reaction equation
Cl.[C:2]([C:6]1[CH:19]=[CH:18][C:9]2[NH:10][C:11]([CH2:13][CH2:14][CH2:15][CH2:16]Cl)=[N:12][C:8]=2[CH:7]=1)([CH3:5])([CH3:4])[CH3:3].[CH:20]([NH2:23])([CH3:22])[CH3:21]>>[C:2]([C:6]1[CH:19]=[CH:18][C:9]2[NH:10][C:11]([CH2:13][CH2:14][CH2:15][CH2:16][NH:23][CH:20]([CH3:22])[CH3:21])=[N:12][C:8]=2[CH:7]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 178440685HCID 178440685, compound

Product 1

HCID 178457182HCID 178457182, compoundYield 51.3%

Procedure

A solution of 5-tert-butyl-2-(4-chloro-butyl)-1H-benzoimidazole hydrochloride (500 mg, 1.66 mmol) in isopropylamine (6 ml, 70.04 mmol) was heated to 80° in a sealed tube overnight. The reaction was cooled to RT and solvent evaporated. The residue was purified by flash column chromatography over silica gel, eluted with MeOH in DCM from 2% to 10% gradually to yield 245 mg (51%) of clean product as a yellow oil; MS (ESI+) for C18H29N3 m/z 1 [M+H]+, 288.50; HPLC purity 99% (ret. time, 1.12 min). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.10 (6H, d, J=6.26 Hz), 1.37 (9H, s), 1.60 (2H, quin, J=7.06 Hz), 1.90 (2H, quin, J=7.25 Hz), 2.66 (2H, t, J=6.79 Hz), 2.82 (1H, spt, J=6.23 Hz), 2.93 (2H, t, J=7.17 Hz), 7.22-7.30 (1H, m), 7.46 (1H, d, J=8.39 Hz), 7.54 (1H, s).

Workup

  1. customsolvent evaporated
  2. customThe residue was purified by flash column chromatography over silica gel
  3. washeluted with MeOH in DCM from 2% to 10% gradually

Sources & evidence

ORD record
ord-4e6a932406294b9ebc7dcf8bc9d44ec0
Source dataset
uspto-grants-2016_07
Patent number
US09394310B2

Reaction notes

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