Hydrochloric Acid → 2-{2-[4-(4-Aminobutyl)phenoxy]ethylamino}acetamide dihydrochloride salt

HRID 1890805Notes

Reaction equation

HRID 1890805 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][NH:21][CH2:22][C:23](=[O:25])[NH2:24])=[CH:14][CH:13]=1)(C)(C)C.[ClH:27]>C1COCC1.O1CCOCC1>[ClH:27].[ClH:27].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][NH:21][CH2:22][C:23]([NH2:24])=[O:25])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58809802(4-{4-[2-(Carbamoylmethylamino)ethoxy]phenyl}butyl)carbamic acid tert-butyl ester

Product 1

HCID 668399752-{2-[4-(4-Aminobutyl)phenoxy]ethylamino}acetamide dihydrochloride salt

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound 3 (0.25 g, 0.68 mmol) was dissolved in THF (3 mL), treated with 4 N HCl in dioxane (10 mL) and the reaction was stirred at room temperature for 2 hours. After this time, TLC analysis indicated a complete reaction. The reaction mixture was concentrated under vacuum, and methanol (2 mL) was added to the resulting residue. The resulting precipitate was collected by vacuum filtration and further dried in a vacuum oven to provide 4 (0.154 g, 67% overall yield for two steps) as a light brown solid. 1H NMR (300 MHz, CD3OD) δ 1.70 (m, 4H), 2.65 (m, 2H), 2.95 (m, 2H), 3.27 (m, 2H), 3.52 (t, 2H), 3.90 (s, 2H), 4.30 (t, 2H), 6.92 (d, 2H), 7.18 (d, 2H). m/z (ESI) 266.

Workup

  1. customa complete reaction
  2. concentrationThe reaction mixture was concentrated under vacuum, and methanol (2 mL)
  3. additionwas added to the resulting residue
  4. filtrationThe resulting precipitate was collected by vacuum filtration
  5. customfurther dried in a vacuum oven
  6. customto provide
  7. custom4 (0.154 g, 67% overall yield for two steps) as a light brown solid

Sources & evidence

ORD record
ord-28325131449f465aad1d39c9773a0c33
Source dataset
uspto-grants-2013_08
Patent number
US08507497B2

Reaction notes

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