Trifluoroacetic acid → 4-(3,4-Dichloro-phenoxy)-[1,4']bipiperidine

HRID 349742Notes

Reaction equation

HRID 349742 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][CH:17]([O:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=3)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:28][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[Cl:27])[O:20][CH:17]1[CH2:16][CH2:15][N:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 112125444-(3,4-Dichlorophenoxy)-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester

Product 1

HCID 223974344-(3,4-Dichloro-phenoxy)-[1,4']bipiperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Step 2 (10.15 g, 23.6 mmol) was dissolved in dichloromethane (150 ml) and trifluoroacetic acid (40 ml, 519 mmol) added and the resultant solution stirred. After 90 minutes the dichloromethane and trifluoroacetic acid were removed on a rotary evaporator. The resultant oil was partitioned between ethyl acetate (100 ml) and 2M aq NaOH (100 ml). The layers were separated and the organics extracted with 10% aq citric acid (100 ml). The layers were separated and the aqueous basified with 2M aq NaOH and extracted with ethyl acetate (200 ml). The organics were dried (MgSO4), filtered and the solvent removed to give the sub-titled product as a pale oil which solidified on standing (4.62 g, 59%; MS: (M+H) 329).

Workup

  1. customAfter 90 minutes the dichloromethane and trifluoroacetic acid were removed on a rotary evaporator
  2. customThe resultant oil was partitioned between ethyl acetate (100 ml) and 2M aq NaOH (100 ml)
  3. customThe layers were separated
  4. extractionthe organics extracted with 10% aq citric acid (100 ml)
  5. customThe layers were separated
  6. extractionextracted with ethyl acetate (200 ml)
  7. dry with materialThe organics were dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed

Sources & evidence

ORD record
ord-60be21f7d98e49dab19b433a97ee0443
Source dataset
uspto-grants-2007_02
Patent number
US07179922B2

Reaction notes

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