Methyl 4-Formylbenzoate → HCID 68292076, compound

HRID 2276926Notes

Reaction equation

HRID 2276926 reaction equation
Cl.Cl.[O:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][C@@H:4]1[C:13]1[CH:25]=[CH:24][C:16]([CH2:17][N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:15][CH:14]=1.[CH3:26][O:27][C:28](=[O:37])[C:29]1[CH:34]=[CH:33][C:32]([CH:35]=O)=[CH:31][CH:30]=1.C([BH3-])#N.[Na+].CCN(C(C)C)C(C)C>CO.C(O)(=O)C>[CH3:26][O:27][C:28](=[O:37])[C:29]1[CH:34]=[CH:33][C:32]([CH2:35][N:21]2[CH2:20][CH2:19][N:18]([CH2:17][C:16]3[CH:15]=[CH:14][C:13]([C@@H:4]4[O:3][C:8]5[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=5[O:6][CH2:5]4)=[CH:25][CH:24]=3)[CH2:23][CH2:22]2)=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 15294Methyl 4-FormylbenzoateHCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 68292670HCID 68292670, compound

Product 1

HCID 68292076HCID 68292076, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-[(S)-4-(2,3-dihydro-benzo[1,4]dioxin-2-yl)-benzyl]-piperazine dihydrochloride (80 mg, 0.21 mmol), 4-formyl-benzoic acid methyl ester (41 mg, 0.25 mmol), sodium cyanoborohydride (26 mg, 0.42 mmol), and DIPEA (0.07 mL, 0.42 mmol) in MeOH (5 mL) is treated with 2 drops of acetic acid. The resulting mixture is stirred at room temperature for 16 h, concentrated, diluted with water, and extracted with ethyl acetate. The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated. The residue is purified by flash chromatography eluting with a gradient of 0-10% MeOH in DCM to give 4-{4-[(S)-4-(2,3-dihydro-benzo[1,4]dioxin-2-yl)-benzyl]-piperazin-1-ylmethyl}-benzoic acid methyl ester.

Workup

  1. concentrationconcentrated
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by flash chromatography
  9. washeluting with a gradient of 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-e2d4b38ffd20476d8e15e90bf9165b82
Source dataset
uspto-grants-2015_09
Patent number
US09133146B2

Reaction notes

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