Acetic Acid → HCID 22049397, compound

HRID 1832972Notes

Reaction equation

HRID 1832972 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:16](=O)C)=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[NH:19]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:26]=[C:27]([N:31]3[CH2:35][CH2:34][CH2:33][C:32]3=[O:36])[CH:28]=[CH:29][CH:30]=2)[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CC(O)=O.C([O-])(O)=O.[Na+]>ClCCCl>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([CH2:16][N:19]3[CH2:20][CH2:21][CH:22]([C:25]4[CH:26]=[C:27]([N:31]5[CH2:35][CH2:34][CH2:33][C:32]5=[O:36])[CH:28]=[CH:29][CH:30]=4)[CH2:23][CH2:24]3)=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 28429721-(9-ethyl-9H-carbazol-3-yl)ethanoneHCID 5049666Sodium triacetoxyborohydrideHCID 22049036HCID 22049036, compound

Product 1

HCID 22049397HCID 22049397, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Prepared by Scheme R and Procedure F. A solution of 1-(9-ethyl-9H-carbazol-3-yl)ethanone (22.3 mg, 0.100 mmol) and 1-[3-(4-piperidinyl)phenyl]-2-pyrrolidinone (27.2 mg, 0.100 mmol) in 1,2-dichloroethane (1.00 mL) was treated with sodium triacetoxyborohydride (63.6 mg, 0.300 mmol) and HOAc (5.70 uL, 0.100 mmol). The mixture was stirred overnight at room temperature. The reaction mixture was treated with a saturated aqueous NaHCO3 solution (10 mL). The aqueous layer was extracted with CH2Cl2 (3×10 mL) and the combined organic layers were washed with brine (10 mL), dried over MgSO4 and concentrated in vacuo. The residue was purified by preparative TLC using 5% of NH3 (2.0 M in methanol) in CH2Cl2 to give the desired product 1-(3-{1-[(9-ethyl-9H-carbazol-3-yl)methyl]-4-piperidinyl}phenyl)-2-pyrrolidinone (4.60 mg, 9.43%): 1H NMR (400 MHz, CDCl3) δ 8.04 (d, 1H, J=7.4 Hz), 7.99 (s, 1H), 7.43–7.28 (m, 5H), 6.96 (d, 1H, J=7.4 Hz), 4.31 (q, 2H, J=6.8 Hz), 3.77 (t, 2H, J=7.3 Hz), 3.70 (s, 2H), 3.06 (d, 2H, J=10.6 Hz), 2.56–2.42 (m, 3H), 2.07 (m, 4H), 1.77 (m, 4H), 1.36 (m, 3H) ESMS m/e: 452.5 (M+H)+.

Workup

  1. customPrepared by Scheme R and Procedure F
  2. extractionThe aqueous layer was extracted with CH2Cl2 (3×10 mL)
  3. washthe combined organic layers were washed with brine (10 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-a7dde199e5724db7a5cda138489a727e
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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