Trifluoroacetic acid → HCID 68678854, compound

HRID 1989065Notes

Reaction equation

HRID 1989065 reaction equation
[CH3:1][N:2]([CH2:4][C:5](Cl)=[O:6])[CH3:3].C(OC(=O)[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:16]=1)(C)(C)C.C(N(CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.O>[NH2:14][C:15]1[CH:16]=[C:17]([CH:21]2[CH2:26][CH2:25][N:24]([C:5](=[O:6])[CH2:4][N:2]([CH3:3])[CH3:1])[CH2:23][CH2:22]2)[CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 70103442-(Dimethylamino)acetyl chlorideHCID 29948324tert-Butyl [3-(piperidin-4-yl)phenyl]carbamate2×

Product 1

HCID 68678854HCID 68678854, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Dimethylamino-acetyl chloride (0.14 g, 0.86 mmol) and (3-piperidin-4-yl-phenyl)-carbamic acid tert-butyl ester (0.20 g, 0.72 mmol) were combined in CH2Cl2 (5 mL) and triethylamine (0.21 g, 2.2 mmol) was added. After 6 h, water (5 mL) was added. The reaction mixture was extracted with CH2Cl2 (3×5 mL) and the combined organic extracts were dried (MgSO4) and concentrated. The compound was found to be unstable on silica and therefore carried on without further purification. (3-Piperidin-4-yl-phenyl)-carbamic acid tert-butyl ester (0.72 mmol) was diluted in CH2Cl2 (3 mL) and TFA (3 mL) was added. After 1 h, the reaction mixture was concentrated. Water (2 mL) was added and the solution was frozen and lyophilized overnight to provide (0.090 g) (48%) of 1-[4-(3-amino-phenyl)-piperidin-1-yl]-2-dimethylamino-ethanone.

Workup

  1. extractionThe reaction mixture was extracted with CH2Cl2 (3×5 mL)
  2. dry with materialthe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. customcarried on without further purification
  5. waitAfter 1 h
  6. concentrationthe reaction mixture was concentrated
  7. additionWater (2 mL) was added
  8. temperaturethe solution was frozen
  9. waitlyophilized overnight

Sources & evidence

ORD record
ord-19f430d55ed9473c9c5fb5ebac4e4645
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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