Triethylamine → HCID 86670527, compound

HRID 1808730Notes

Reaction equation

HRID 1808730 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.[F:22][C:23]([F:35])([F:34])[C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>CN(C)C1C=CN=CC=1.ClCCl>[F:35][C:23]([F:22])([F:34])[C:24]1[CH:25]=[CH:26][C:27]([S:30]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)(=[O:32])=[O:31])=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 27773994-(Trifluoromethyl)benzenesulfonyl chloride

Product 1

HCID 86670527HCID 86670527, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirring dichloromethane (50 mL) solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (3.90 g, 19.4 mmol), 4-(dimethylamino)pyridine (0.23 g, 1.9 mmol), and triethylamine (8.0 mL, 57 mmol) was added 4-(trifluoromethyl)benzenesulfonyl chloride (4.75 g, 19.4 mmol). The reaction mixture was stirred for two hours at room temperature. The reaction was quenched with 1.0 M hydrochloric acid (100 mL) and extracted with diethyl ether (2×250 mL). The combined organic extracts were dried (magnesium sulfate), filtered and concentrated in vacuo to afford the crude product. It was used in the subsequent step without further purification. 1H NMR (500 MHz, CDCl3) δ 8.06 (d, J=8.2 Hz, 2H), 7.83 (d, J=8.2 Hz, 2H), 4.79 (tt, J=7.6, 3.6 Hz, 1H), 3.62 (ddd, J=13.6, 7.4, 4.0 Hz, 2H), 3.27 (ddd, J=13.8, 7.8, 3.9 Hz, 2H), 1.86-1.79 (m, 2H), 1.75-1.68 (m, 2H), 1.44 (s, 9H).

Workup

  1. customThe reaction was quenched with 1.0 M hydrochloric acid (100 mL)
  2. extractionextracted with diethyl ether (2×250 mL)
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6462f019b0cc47d996cb0a3f72a7ff9c
Source dataset
uspto-grants-2013_01
Patent number
US08361994B2

Reaction notes

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