Water → N-(3,4-Dichlorophenyl)-3-azaspiro[5.5]undecan-9-amine

HRID 554477Notes

Reaction equation

HRID 554477 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][CH:16]([NH: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.FC(F)(F)C(O)=O.O.[OH-].[Na+]>ClCCl>[CH2:12]1[C:11]2([CH2:14][CH2:15][CH:16]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)[CH2:17][CH2:18]2)[CH2:10][CH2:9][NH:8][CH2:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 674592189-(3,4-Dichloro-phenylamino)-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester

Product 1

HCID 16006654N-(3,4-Dichlorophenyl)-3-azaspiro[5.5]undecan-9-amineYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of 9-(3,4-dichloro-phenylamino)-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (258 mg, 0.624 mmol) in dichloromethane (10 mL) a solution of trifluoroacetic acid (4 mL) in dichloromethane (5 mL) was added. The mixture was stirred a room temperature over night. Water was added followed by sodium hydroxide 3 M to pH 9-10. The aqueous layer was extracted with dichloromethane (4×40 mL). The combined organic layers were washed with brine, dried with sodium sulphate and evaporated to give (3-aza-spiro[5.5]undec-9-yl)-(3,4-dichloro-phenyl)-amine (164 mg 84%) as a brownish solid. Mp. 128-132° C.

Workup

  1. additionwas added
  2. extractionThe aqueous layer was extracted with dichloromethane (4×40 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-bc70750dba1a4cd681de62352c75f201
Source dataset
uspto-grants-2011_11
Patent number
US08049012B2

Reaction notes

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