Hydrochloric Acid → HCID 58137305, compound

HRID 1424570Notes

Reaction equation

HRID 1424570 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.N#N.Cl>C1COCC1>[C:1]([N:9]1[CH2:14][CH2:13][CH2:12][C:11]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 7498Benzyl BromideHCID 2724682Lithium diisopropylamideHCID 3784394Ethyl 1-benzoyl-3-piperidinecarboxylate

Product 1

HCID 58137305HCID 58137305, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl 1-benzoylpiperidine-3-carboxylate (9.22 g, 35 mmol) in dry THF (55 mL) at −78° C. was added dropwise LDA (39 mmol, 1.1 eq) in 45 mL of dry THF. After addition, the reaction was stirred for 1 h. Then benzyl bromide (6.54 g, 39 mmol, 1.1 eq) was added dropwise under the an atmosphere of N2. The reaction was stirred for another 3 h. The solution was added dropwise 5% HCl at 0° C. and concentrated. The aqueous residue was extracted with CH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4 and evaporated to afford ethyl 1-benzoyl-3-benzylpiperidine-3-carboxylate (11.16 g, 91%). 1H NMR (CD3OD, 400 MHz): δ=1.30 (t, 3H), 1.50˜1.55 (m, H), 2.75 (m, 2H), 3.65 (m, 4H), 4.09 (m, 2H), 7.08 (m, 2H), 7.22 (m, 3H), 7.48 (m, 5H).

Workup

  1. additionAfter addition
  2. stirringThe reaction was stirred for another 3 h
  3. concentrationconcentrated
  4. extractionThe aqueous residue was extracted with CH2Cl2
  5. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-1a02335a08b04c5491a5be22aa2dc281
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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