Hydrochloric Acid → 2-[4-(4-Aminobutyl)phenoxy]-N-(1H-imidazol-2-yl)acetamide dihydrochloride

HRID 132569Notes

Reaction equation

HRID 132569 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][C:20](=[O:27])[NH:21][C:22]2[NH:23][CH:24]=[CH:25][N:26]=2)=[CH:14][CH:13]=1)(C)(C)C.[ClH:29]>>[ClH:29].[ClH:29].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([NH:21][C:22]2[NH:26][CH:25]=[CH:24][N:23]=2)=[O:27])=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 21031134(4-{4-[(1H-Imidazol-2-yl-carbamoyl)methoxy]phenyl}butyl)carbamic acid tert-butyl ester

Product 1

HCID 220544322-[4-(4-Aminobutyl)phenoxy]-N-(1H-imidazol-2-yl)acetamide dihydrochloride

Procedure

(4-{4-[(1H-Imidazol-2-yl-carbamoyl)methoxy]phenyl}butyl)carbamic acid tert-butyl ester 34 (950 mg, 2.45 mmol) was treated with HCl (4 M in dioxane, 24 mL, 96 mmol) at room temperature for 12 h. The reaction mixture was concentrated in vacuo and further co-evaporated with dichloromethane and methanol, and dried under high vacuum. The desired product was obtained as a white solid (779 mg, 98%) and used directly without further purification. 1H NMR (300 MHz, CD3OD) δ 1.59-1.74 (m, 4H), 2.55-2.67 (m, 2H), 2.85-2.98 (m, 2H), 4.80 (s, 2H), 7.00 (d, 2H), 7.18 (d, 2H), 7.19 (s, 2H). m/z (ESI): 289 [C15H20N4O2+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and further co-evaporated with dichloromethane and methanol
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-d36d2142174940578a72add7d27aca08
Source dataset
uspto-grants-2008_06
Patent number
US07388013B2

Reaction notes

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