Acetic Acid → 1-(2-[(2R)-4-(6-Fluoro-1-naphthyl)-2-methyl-piperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-carbonitrile

HRID 2056756Notes

Reaction equation

HRID 2056756 reaction equation
O=[CH:2][CH2:3][CH:4]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]#[N:15])=[CH:13][C:8]=2[CH2:7][CH2:6][O:5]1.[F:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23]([N:27]1[CH2:32][CH2:31][NH:30][C@H:29]([CH3:33])[CH2:28]1)=[CH:22][CH:21]=[CH:20]2.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[F:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23]([N:27]1[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH:4]3[C:9]4[CH:10]=[CH:11][C:12]([C:14]#[N:15])=[CH:13][C:8]=4[CH2:7][CH2:6][O:5]3)[C@H:29]([CH3:33])[CH2:28]1)=[CH:22][CH:21]=[CH:20]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydride2×HCID 69307275(2R)-4-(6-fluoro-1-naphthyl)-2-methylpiperazineHCID 865960151-(2-Oxoethyl)-3,4-dihydro-1H-2-benzopyran-6-carbonitrile

Product 1

HCID 693073181-(2-[(2R)-4-(6-Fluoro-1-naphthyl)-2-methyl-piperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1-(2-oxoethyl)-3,4-dihydro-1H-2-benzopyran-6-carbonitrile (0.454 g, 2.26 mmol) in methanol (30 mL) was added (3R)-1-(6-fluoro-1-naphthyl)-3-methylpiperazine (0.61 g, 2.49 mmol), and the mixture stirred for 10 min. Sodium cyanoborohydride (0.157 g, 2.49 mmol) and acetic acid (0.25 mL) were added and the mixture stirred for 18 h. A further portion of sodium cyanoborohydride (0.20 g) was added and the reaction stirred for 6 h. The mixture was quenched with water, and the solvent removed in vacuo. Water was added and the mixture extracted with chloroform, the organic extracts dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by preparative LC-MS to yield the title compound as a yellow oil.

Workup

  1. stirringthe mixture stirred for 18 h
  2. stirringthe reaction stirred for 6 h
  3. customThe mixture was quenched with water
  4. customthe solvent removed in vacuo
  5. additionWater was added
  6. extractionthe mixture extracted with chloroform
  7. dry with materialthe organic extracts dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe crude product was purified by preparative LC-MS

Sources & evidence

ORD record
ord-5903f0d05655498882700973ba6bf066
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

Loading…