Hydrochloric Acid → HCID 68996322, compound

HRID 2059695Notes

Reaction equation

HRID 2059695 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-5032b0cadb3f4ebaa6765f2a0b2185ae
Source dataset
uspto-grants-2012_10
Patent number
US08278301B2

Reaction notes

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