Hydrochloric Acid → HCID 68996322, compound

HRID 1987985Notes

Reaction equation

HRID 1987985 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([N:10]1[CH:15]2[CH2:16][CH2:17][CH2:18][CH:11]1[CH2:12][CH:13]([NH:19]C(=O)OC(C)(C)C)[CH2:14]2)[CH3:9].[ClH:27].C(OCC)C>C(Cl)Cl>[ClH:27].[ClH:27].[CH2:8]([N:10]1[CH:11]2[CH2:18][CH2:17][CH2:16][CH:15]1[CH2:14][CH:13]([NH2:19])[CH2:12]2)[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 68996667HCID 68996667, compound

Product 1

HCID 68996322HCID 68996322, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 mL) was added to a solution of tert-butyl 9-ethyl-9-azabicyclo[3.3.1]nonan-3-ylcarbamate from Step C (50 mg, 0.19 mmol) in methylene chloride (1 mL) at room temperature and the mixture was stirred under nitrogen for 2 h. The mixture was concentrated and the residue was dissolved in methanol (1 mL). HCl in diethyl ether (1.0 M, 2.0 mL, 2.0 mmol) was added dropwise at room temperature and the mixture was stirred for 5 min. The mixture was concentrated again and dried under vacuum overnight to give 9-ethyl-9-azabicyclo[3.3.1]nonan-3-amine dihydrochloride (45 mg, 99%) as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 9.75 (br s, 1H), 8.39 (br s, 3H), 4.14 (br s, 1H), 3.73-3.71 (m, 2H), 3.25 (q, J=7.0 Hz, 2H), 2.55-2.48 (m, 2H), 2.05-1.95 (m, 3H), 1.80-1.76 (m, 1H), 1.50-1.22 (m, 7H); MS (ESI+) m/z 169 (M+H).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in methanol (1 mL)
  3. stirringthe mixture was stirred for 5 min
  4. concentrationThe mixture was concentrated again
  5. customdried under vacuum overnight

Sources & evidence

ORD record
ord-6d35eb3fc3ab4c71ac9fcb1ee622c4b5
Source dataset
uspto-grants-2009_06
Patent number
US07553846B2

Reaction notes

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