Methylamine hydrochloride → HCID 15322639, compound

HRID 35796Notes

Reaction equation

HRID 35796 reaction equation
Cl.[CH3:2][NH2:3].C[Al](C)C.[Cl:8][CH2:9][CH2:10][S:11][CH:12]([S:17][CH2:18][CH2:19][Cl:20])[C:13](OC)=[O:14]>C1C=CC=CC=1>[CH3:2][NH:3][C:13](=[O:14])[CH:12]([S:17][CH2:18][CH2:19][Cl:20])[S:11][CH2:10][CH2:9][Cl:8]

Participants

5

Reactant 3

HCID 6364545Methylamine hydrochlorideHCID 15322638HCID 15322638, compoundHCID 16682925Trimethylaluminum

Product 1

HCID 15322639HCID 15322639, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a stirred suspension of methylamine hydrochloride (3.464 g; 0.051 mol) in 60 mL of dry benzene under nitrogen at room temperature was added trimethylaluminum (Aldrich, 25.65 mL of 2.0M solution in toluene). After gas evolution ceased (30 min) a solution of the ester 4b (4.500 g; 0.017 mol in 10 mL of dry benzene was added and the mixture was warmed to 50° C. After 21 h, the mixture was allowed to cool to room temperature and was then quenched by dropwise addition of 60 mL of 1.0 N HCl. The mixture was extracted several times with ethyl acetate and the combined extracts were dried (MgSO4) and concentrated under vacuum. Flash chromatography on silica gel (eluent: 2/3 ethyl acetate/hexanes) gave 2.849 g (64%) of 4c, mp 82°-84° C.

Workup

  1. custom(30 min)
  2. temperatureto cool to room temperature
  3. customwas then quenched by dropwise addition of 60 mL of 1.0 N HCl
  4. extractionThe mixture was extracted several times with ethyl acetate
  5. dry with materialthe combined extracts were dried (MgSO4)
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-95b4284c828e48aeaa4e8b13eebd21e3
Source dataset
uspto-grants-1995_05
Patent number
US05411856

Reaction notes

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