Water → 1-Hexanoic acid-[1-(3-methoxyphenyl)-2-(1-methyl-2-pyrrolidinyl)-ethyl]-ester

HRID 2049662Notes

Reaction equation

HRID 2049662 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:17]([OH:25])[CH2:18][CH:19]2[CH2:23][CH2:22][CH2:21][N:20]2[CH3:24])[CH:14]=[CH:15][CH:16]=1.C(N(CC)CC)C.O>C(Cl)Cl>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:17]([O:25][C:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:18][CH:19]2[CH2:23][CH2:22][CH2:21][N:20]2[CH3:24])[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 67340Hexanoyl chlorideHCID 30543491-(3-Methoxyphenyl)-2-(1-methylpyrrolidin-2-yl)ethan-1-ol

Product 1

HCID 203441291-Hexanoic acid-[1-(3-methoxyphenyl)-2-(1-methyl-2-pyrrolidinyl)-ethyl]-esterYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.7 g of hexanoyl chloride in 10 ml of methylene chloride is added drop by drop to a mixture of 1.17 g of 1-(3-methoxyphenyl)-2-(1-methyl-2-pyrrolidinyl)-ethanol and 0.5 g of triethyl amine in 20 ml methylene chloride. The mixture is stirred for 2 hours and subsequently treated with water. The organic phase is separated, dried over sodium sulphate and concentrated. There are obtained 1.5 g of the title compound as tough, light oil.

Workup

  1. customThe organic phase is separated
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d578435671164de881bedb78e212d1c8
Source dataset
uspto-grants-1980_04
Patent number
US04198424

Reaction notes

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