Hydrochloric Acid → 3-Methoxy-4-(1-pyrrolidinyl)methylbenzoic acid hydrochloride

HRID 1264081Notes

Reaction equation

HRID 1264081 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[C:6]([O:8]C)=[O:7].COC1C=C(C=CC=1C)C(OC)=O.N1CCCC1.[OH-].[Na+].[ClH:39]>C(O)C>[ClH:39].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[C:6]([OH:8])=[O:7]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 591123Benzoic acid, 3-methoxy-4-methyl-, methyl esterHCID 10824510Methyl 3-methoxy-4-(pyrrolidin-1-ylmethyl)benzoate

Product 1

HCID 696919043-Methoxy-4-(1-pyrrolidinyl)methylbenzoic acid hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 3-methoxy-4-[(1-pyrrolidinyl)methyl]benzoate (prepared by bromination of methyl 3-methoxy-4-methyl-benzoate by the procedure of Example 1, Part A, followed by treatment with pyrrolidine) (11.56 g, 46.4 mmol), was combined with sodium hydroxide (3.71 g 92.7 mmol, 2.00 eq.) in absolute ethanol (95 mL). After 72 h, the reaction mixture was made acidic to pH 1 by the addition of conc. HCl. The solvent was removed under reduced pressure to give the corresponding acid hydrochloride as a white solid (17.92 g, 99%).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a8bd671062a94d42a939da29d742ee94
Source dataset
uspto-grants-2003_04
Patent number
US06541499B1

Reaction notes

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