Triethylamine → HCID 69834427, compound

HRID 1355568Notes

Reaction equation

HRID 1355568 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 (3x5 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), 1.00-0.91 (m, 1H), 0.59-0.49 (comp, 2H), 0.19-0.11 (comp, 1 H); 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 (3x5 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by flash chromatography with hexanes/EtOAc (1:1)

Sources & evidence

ORD record
ord-2886d1bd8fc448fdb36d0905f1b52b74
Source dataset
uspto-grants-2003_07
Patent number
US06586431B1

Reaction notes

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