Methylamine → HCID 20545899, compound

HRID 2059326Notes

Reaction equation

HRID 2059326 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH2:20][CH:21]4[O:23][CH2:22]4)=[CH:16][CH:17]=3)[C:12](=[O:24])[C:11](C)(C)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:27][NH2:28]>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH2:20][CH:21]([OH:23])[CH2:22][NH:28][CH3:27])=[CH:16][CH:17]=3)[C:12](=[O:24])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 20545914HCID 20545914, compound

Product 1

HCID 20545899HCID 20545899, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 4-(3,4-dichlorophenyl)-7-(2,3-epoxypropoxy)-2,2-dimethyl-1-tetralone (3.2 g) in ethanol (30 ml) was added a solution of methylamine (10 ml) in ethanol (10 ml) and the mixture left to stand overnight. The solvent was removed and the residue shaken with ether-dilute hydrochloric acid. The aqueous layer was separated, basified, extracted with ether and the extract dried (MgSO4). Evaporation gave the product as the free base, which was converted to the hydrochloride salt. Recrystallisation from petrol/ether gave 4-(3,4-dichlorophenyl)-7-(2-hydroxy-3-methylaminopropoxy)-1-tetralone hydrochloride as white crystals (2.5 g, 72%) m.p. 105°-10°(dec).

Workup

  1. waitthe mixture left
  2. customThe solvent was removed
  3. customThe aqueous layer was separated
  4. extractionextracted with ether
  5. dry with materialthe extract dried (MgSO4)
  6. customEvaporation
  7. customgave the product as the free base, which
  8. customRecrystallisation from petrol/ether

Sources & evidence

ORD record
ord-f00a85c5683b4841a02d8e5e95be8ebb
Source dataset
uspto-grants-1982_03
Patent number
US04322370

Reaction notes

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