Benzaldehyde → HCID 20284821, compound

HRID 127510Notes

Reaction equation

HRID 127510 reaction equation
[NH2:1][CH2:2][CH:3]1[C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[S:6][CH2:5][CH2:4]1.[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>CO.C([BH3-])#N.[Na+]>[CH2:16]([NH:1][CH2:2][CH:3]1[C:15]2[C:7](=[N:8][C:9]3[C:14]=2[CH2:13][CH:12]=[CH:11][CH:10]=3)[S:6][CH2:5][CH2:4]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 30560881-(2,3,4,9-Tetrahydrothiopyrano[2,3-b]indol-4-yl)methanamine

Product 1

HCID 20284821HCID 20284821, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 5003444Sodium cyanoborohydrideSolvent

Procedure

To a solution of 4-aminomethyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole (150 mg) in methanol (5 ml) are added a solution of benzaldehyde (76 mg) in methanol (1.5 ml) and sodium cyanoborohydride (132 mg). The mixture is adjusted to pH 7 with a solution of hydrochloride in methanol, stirred at room temperature for 1 hour and evaporated to remove the solvent. The residue is dissolved in ether, washed with a 10% aqueous solution of sodium hydroxide and a saline solution, dried and evaporated to give the title compound (210 mg).

Workup

  1. customevaporated
  2. customto remove the solvent
  3. dissolutionThe residue is dissolved in ether
  4. washwashed with a 10% aqueous solution of sodium hydroxide
  5. customa saline solution, dried
  6. customevaporated

Sources & evidence

ORD record
ord-84dee13c01884284825e175ee3d51cf3
Source dataset
uspto-grants-1981_03
Patent number
US04256640

Reaction notes

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