Trifluoroacetic acid → 9-(3,4-Dichloro-phenoxy)-3-aza-spiro[5.5]undecane trifluoroacetic acid salt

HRID 554470Notes

Reaction equation

HRID 554470 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][CH:16]([O:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)[CH2:15][CH2:14]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31]>ClCCl>[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31].[Cl:27][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[Cl:26])[O:19][CH:16]1[CH2:15][CH2:14][C:11]2([CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 674634929-(3,4-Dichloro-phenoxy)-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester

Product 1

HCID 674599119-(3,4-Dichloro-phenoxy)-3-aza-spiro[5.5]undecane trifluoroacetic acid saltYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9-(3,4-Dichloro-phenoxy)-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (340 mg, 0.82 mmol) was dissolved in dichloromethane (8 mL) and cooled on an ice bath. Trifluoroacetic acid (2 mL) was added and stirred for 2 h at room temperature. Evaporation followed by co-evaporation with toluene and ethyl acetate gave a solid compound. The compound was washed with diethyl ether to give 222 mg (63%) of 9-(3,4-dichloro-phenoxy)-3-aza-spiro[5.5]undecane trifluoroacetic acid salt as a white crystalline compound. Mp. 139, 6-141.2° C.

Workup

  1. temperaturecooled on an ice bath
  2. customEvaporation
  3. customgave a solid compound
  4. washThe compound was washed with diethyl ether

Sources & evidence

ORD record
ord-78cdb648a9f94a79a7565de22674e30d
Source dataset
uspto-grants-2011_11
Patent number
US08049012B2

Reaction notes

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