Hydrochloric Acid → 6-Amino-N-(pyridin-3-yl)hexanoamide Dihydrochloride

HRID 1255100Notes

Reaction equation

HRID 1255100 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:21])[NH:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)(C)(C)C.[ClH:23]>C(Cl)Cl.O1CCOCC1>[ClH:23].[ClH:23].[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([NH:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:21]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66810297(5-(Pyridin-3-ylcarbamoyl)pentyl]carbamic acid tert-butyl ester

Product 1

HCID 668104466-Amino-N-(pyridin-3-yl)hexanoamide Dihydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To an ice-cold mixture of (5-(Pyridin-3-ylcarbamoyl)pentyl)carbamic acid tert-butyl ester (3, 3.07 g, 10 mmole) in methylene chloride (30 mL) was added a solution of HCl in dioxane (4M, 10 mL). The mixture was stirred at room temperature overnight. The separated solid was filtered, washed with methylene chloride, dried in vacuum oven to give the product 4 as the hydrochloride salt (2.7 g, 96%). The 1H NMR spectrum of the pure solid was consistent with structure 4. 1H NMR (D2O) δ 9.20 (s, 2H), 7.91 (m, 1H), 2.90 (t, 2H), 2.42 (t, 2H), 2.62 (m, 4H), 1.36 (m, 2H).

Workup

  1. filtrationThe separated solid was filtered
  2. washwashed with methylene chloride
  3. customdried in vacuum oven

Sources & evidence

ORD record
ord-4a383a7a40f34099a885cf5cff819055
Source dataset
uspto-grants-2013_06
Patent number
US08455688B2

Reaction notes

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