Trifluoroacetic acid → HCID 22913027, compound

HRID 2060017Notes

Reaction equation

HRID 2060017 reaction equation
[C:1]1([CH2:7][N:8]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>ClCCl>[C:23]1([CH2:22][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 59444161HCID 59444161, compound

Product 1

HCID 22913027HCID 22913027, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl 4-[bis(phenylmethyl)amino]-1-piperidinecarboxylate D74 (160 g, 420 mmol) was dissolved in dichloromethane (DCM) (1 L) and TFA (188 mL, 2443 mmol) was added dropwise at room temperature. The resulting mixture was stirred for 3 h then further 100 mL of TFA was added and stirred for 2 h. The mixture was concentrated under reduced pressure and the residue treated with saturated solution NaHCO3 (1.5 L) and NaOH (3M solution; 200 mL) to basic pH. The aqueous phase was extracted with DCM (2×1.5 L). Combined organic layers were diluted with ethyl acetate (100 mL), washed with water (1×1 L) and brine (1×1 L) then dried on Na2SO4 and concentrated to obtain title material (118 g; 100%).

Workup

  1. stirringstirred for 2 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionthe residue treated with saturated solution NaHCO3 (1.5 L) and NaOH (3M solution; 200 mL) to basic pH
  4. extractionThe aqueous phase was extracted with DCM (2×1.5 L)
  5. additionCombined organic layers were diluted with ethyl acetate (100 mL)
  6. washwashed with water (1×1 L) and brine (1×1 L)
  7. customthen dried on Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1b259c50c004481e90b3c4494e8e8f2f
Source dataset
uspto-grants-2012_10
Patent number
US08278328B2

Reaction notes

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