1,4-Dioxane hydrochloride → [1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethyl]-(3-fluoro-benzyl)-(2-piperazin-1-yl-ethyl)-amine

HRID 2101497Notes

Reaction equation

HRID 2101497 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]([CH2:25][C:26]2[N:27]([CH2:31][C:32]3[CH:37]=[C:36]([Cl:38])[CH:35]=[C:34]([Cl:39])[CH:33]=3)[CH:28]=[CH:29][N:30]=2)[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>>[Cl:39][C:34]1[CH:33]=[C:32]([CH:37]=[C:36]([Cl:38])[CH:35]=1)[CH2:31][N:27]1[CH:28]=[CH:29][N:30]=[C:26]1[CH2:25][N:16]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=1)[CH2:15][CH2:14][N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 57801494HCID 57801494, compound

Product 1

HCID 11949835[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethyl]-(3-fluoro-benzyl)-(2-piperazin-1-yl-ethyl)-amineYield 98%

Procedure

A mixture of 4-{2-[[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethyl]-(3-fluoro-benzyl)-amino]-ethyl}-piperazine-1-carboxylic acid tert-butyl ester (92 mg, 0.16 mmol) and 4N HCl/dioxane (5 mL) was stirred at ambient temperature for 2 h. The solvent was removed in vacuo and water (5 mL) added. The pH of the solution was adjusted to pH 9 by addition of 1N NaOH and the mixture extracted with CH2Cl2 (2×20 mL). The combined CH2Cl2 extracts were dried over Na2SO4 and concentrated in vacuo to afford [1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethyl]-(3-fluoro-benzyl)-(2-piperazin-1-yl-ethyl)-amine (74 mg, 98%) as colorless a viscous oil: ESI MS m/z 476 [C24H28Cl2FN5+H]+.

Workup

  1. customThe solvent was removed in vacuo and water (5 mL)
  2. additionadded
  3. additionThe pH of the solution was adjusted to pH 9 by addition of 1N NaOH
  4. extractionthe mixture extracted with CH2Cl2 (2×20 mL)
  5. dry with materialThe combined CH2Cl2 extracts were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a89ece525ab45f0924477bf61925591
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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