N-methyl-2-pyrrolidone → HCID 21071658, compound

HRID 1371930Notes

Reaction equation

HRID 1371930 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:12][CH2:13][NH2:14])=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.[CH2:15]([O:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=O)[CH2:16][CH3:17].[BH4-].[Na+].[CH3:29]N1CCCC1=O>ClCCl.C(O)(=O)C.CO>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:12][CH2:13][N:14]([CH2:22][C:21]3[CH:24]=[CH:25][CH:26]=[C:19]([O:18][CH2:15][CH2:16][CH3:17])[CH:20]=3)[CH3:29])=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidone2×HCID 27604693-PropoxybenzaldehydeHCID 4311764Sodium borohydrideHCID 54594690HCID 54594690, compound

Product 1

HCID 21071658HCID 21071658, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10129899Acetic acid methanolSolvent

Procedure

Combine N-methyl-N-(2-(6-fluoro-1-methyl-1H-indol-3-yl)ethylamine (0.2 mmol) in 1-methyl-2-pyrrolidinone (0.5 mL) and 3-propyloxybenzaldehyde (0.32 mmol) in dichloromethane (1 mL) and rotate. After overnight rotation, add sodium borohydride (1.0 mmol) as a stock solution in 1-methyl-2-pyrrolidinone (0.5 mL) and rotate. After rotation for 3 h, dilute the reaction mixture with 1 mL of 10% acetic acid/methanol, and directly apply the resulting solution to a 2 g SCX column. After thoroughly washing with methanol, elute the column with 2 M ammonia-methanol and concentrate the eluent to a residue, which was further purified by Gilson UV prep system.

Workup

  1. waitAfter rotation for 3 h
  2. washAfter thoroughly washing with methanol
  3. washelute the column with 2 M ammonia-methanol
  4. concentrationconcentrate the eluent to a residue, which
  5. customwas further purified by Gilson UV prep system

Sources & evidence

ORD record
ord-0ce01908c6c14d0aa992855115f7a950
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

Loading…