HCID 86639103, compound → HCID 66811513, compound

HRID 1099199Notes

Reaction equation

HRID 1099199 reaction equation
FC(F)(F)C([O-])=O.[CH2:8]([NH:15][C:16]([CH:18]1[CH:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:22][CH2:21][CH2:20][NH2+:19]1)=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1>[C:9]1([CH2:8][NH:15][CH2:16][CH:18]2[CH:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:22][CH2:21][CH2:20][NH:19]2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 1

HCID 86639103HCID 86639103, compound

Product 1

HCID 66811513HCID 66811513, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 2-[(benzylamino)carbonyl]-3-phenylpiperidinium trifluoroacetate (604 mg, 1.48 mmol) in THF (2 ml) at 0° C. was added 2M borane-THF complex in THF (7.5 ml, 14.8 mmol). The reaction was allowed to stir for 18 h. Additional 2M borane-THF complex in THF (1.5 ml, 2.96 mmol) was added to the reaction mixture and allowed to stir for an additional 24 h. The reaction was quenched with methanol, concentrated in vacuo, and concentrated again from 4M HCl in dioxane. The crude product was purified via reverse phase preparative HPLC to yield 1-phenyl-N-[(3-phenylpiperidin-2-yl)methyl]methanamine (20%). 1H NMR (400 MHz, CD3OD) δ 7.42-7.28 (m, 10H), 4.05 (m, 2H), 3.82 (m, 1H), 3.58 (d, J=10.9 Hz, 0.4H), 3.38 (m, 2H), 3.21 (m, 0.6H), 2.96 (m, 1H), 2.20 (m, 1H), 1.97 (m, 3H).

Workup

  1. stirringto stir for an additional 24 h
  2. customThe reaction was quenched with methanol
  3. concentrationconcentrated in vacuo
  4. concentrationconcentrated again from 4M HCl in dioxane
  5. customThe crude product was purified via reverse phase preparative HPLC

Sources & evidence

ORD record
ord-66b64960eb5c45e78bb48a00141b28cc
Source dataset
uspto-grants-2012_03
Patent number
US08143405B2

Reaction notes

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