Dimethylamine, hydrochloride → HCID 20284796, compound

HRID 127518Notes

Reaction equation

HRID 127518 reaction equation
Cl.[CH3:2][NH:3][CH3:4].C[O-].[Na+].[CH:8]([CH:10]1[C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:14]=2[S:13][CH2:12][CH2:11]1)=O>CO.O1CCCC1.C([BH3-])#N.[Na+]>[CH3:2][N:3]([CH2:8][CH:10]1[C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:14]=2[S:13][CH2:12][CH2:11]1)[CH3:4]

Participants

7

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 10942334Sodium MethoxideHCID 202847884-Formyl-9-phenyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole

Product 1

HCID 20284796HCID 20284796, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 5003444Sodium cyanoborohydrideSolvent

Procedure

Dimethylamine hydrochloride (1.74 g) is dissolved in absolute methanol (18 ml) and sodium methoxide (813 mg) is added thereto. To the solution are added a solution of the product of the above (1), (1.1 g) in tetrahydrofuran (10 ml) and sodium cyanoborohydride (1 g). The mixture is stirred at room temperature overnight and evaporated after addition of an aqueous solution (4 ml) of sodium hydroxide. The residue is extracted with ether after addition of water and a 10% aqueous solution of sodium hydroxide. The extract is condensed to give the title compound as an oil (1.10 g). The oil is treated with L-tartaric acid (443 mg) in ethanol to give the tartrate (750 mg) melting at 172°-177° C. (decomp.).

Workup

  1. customevaporated
  2. additionafter addition of an aqueous solution (4 ml) of sodium hydroxide
  3. extractionThe residue is extracted with ether
  4. additionafter addition of water
  5. customcondensed

Sources & evidence

ORD record
ord-59a831f2da4f413b8103b41dea7ee8aa
Source dataset
uspto-grants-1981_03
Patent number
US04256640

Reaction notes

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