Triethylamine → HCID 69834427, compound

HRID 1633541Notes

Reaction equation

HRID 1633541 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][CH2:8][C:7]([C:18]3[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=3)([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[CH2:6]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:32](Cl)(=[O:35])[CH2:33][CH3:34]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:1]1([CH2:4][N:5]2[CH2:10][CH2:9][CH2:8][C:7]([C:18]3[CH:19]=[C:20]([O:24][C:32](=[O:35])[CH2:33][CH3:34])[CH:21]=[CH:22][CH:23]=3)([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[CH2:6]2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 18507127HCID 18507127, compound

Product 1

HCID 69834427HCID 69834427, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(1-cyclopropylmethyl-3-p-tolyl-piperidin-3-yl)-phenol (65 mg, 0.15 mmol) in CH2Cl2 (2 ml) at room temperature were added DMAP (18 mg, 0.15 mmol), triethylamine (0.071 mL, 0.52 mmol) and propionyl chloride (0.038 mL, 0.45 mmol). The reaction mixture was stirred at room temperature for 12 hours. The reaction was partitioned between 5 mL CH2Cl2 and 5 mL of aqueous saturated NaHCO3. The aqueous layer was washed with CH2Cl2 (3×5 mL), dried over Na2SO4 and concentrated. Purification by flash chromatography with hexanes/EtOAc (1:1) afforded 58 mg of propionic acid 3-(1-cyclopropylmethyl-3-p-tolyl-piperidin-3-yl)-phenyl ester. 1HNMR (400 MHz, CDCl3) δ 7.33 (d, 2H), 7.26-7.19 (comp, 3H), 7.16-7.03 (comp, 2H), 6.89-6.86 (m, 1H), 3.59-3.43 (comp, 2H), 3.35-3.19 (comp, 2H), 2.59-2.53 (q, 2H), 2.52-2.41 (comp, 2H), 2.27-2.18 (comp, 4H), 1.57-1.44 (comp, 2H), 1.31-1.19 (t, 3H), 1.18-1.09 (comp, 3H), 1.08-1.01 (comp, 3H), 100-0.91 (m, 1H), 0.59-0.49 (comp, 2H), 0.19-0.11 (comp, 1H); MS (M+1) 463.3.

Workup

  1. customThe reaction was partitioned between 5 mL CH2Cl2 and 5 mL of aqueous saturated NaHCO3
  2. washThe aqueous layer was washed with CH2Cl2 (3×5 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by flash chromatography with hexanes/EtOAc (1:1)

Sources & evidence

ORD record
ord-94c2cd88350d46bfb247801c0b2b097f
Source dataset
uspto-grants-2003_01
Patent number
US06503905B1

Reaction notes

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