Methylamine → HCID 21423144, compound

HRID 259122Notes

Reaction equation

HRID 259122 reaction equation
[CH2:1]1[C:6]2[S:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:5]=2[CH2:4][CH2:3][O:2]1.[CH2:14](Cl)[CH3:15].[CH3:17][NH2:18]>CO>[CH3:17][NH:18][CH2:14][CH2:15][CH:1]1[C:6]2[S:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:5]=2[CH2:4][CH2:3][O:2]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 70631266HCID 70631266, compound

Product 1

HCID 21423144HCID 21423144, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3,4-dihydro-1H-[1]benzothieno[2,3-c]pyran-1-ethyl chloride (6.0 g), described in Example 35, and a saturated solution of methylamine in dry methanol (75 ml) is heated in a pressure bottle at 60° C. for 2 hr. The mixture is kept at room temperature for 2 days and then evaporated to dryness. The residue is dissolved in dilute hydrochloric acid and washed with ether. The free base is then liberated from the aqueous phase by the addition of 5% sodium hydroxide solution and extracted with ether. The extract is dried and concentrated to give the title compound, λmaxEtOH 231 nm (29,600), 261 nm (7580), 290 nm (2960), 298 nm (3140); nmr (CDCl3) δ 2.25, 2.86, 5.00.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue is dissolved in dilute hydrochloric acid
  3. washwashed with ether
  4. additionThe free base is then liberated from the aqueous phase by the addition of 5% sodium hydroxide solution
  5. extractionextracted with ether
  6. customThe extract is dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2fa7b569e0574d1cae2c89deb96a0672
Source dataset
uspto-grants-1977_07
Patent number
US04036842

Reaction notes

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