Formaldehyde → HCID 68817511, compound

HRID 735193Notes

Reaction equation

HRID 735193 reaction equation
[CH2:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[C:8]([S:14][C:15]4[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=4)[C:7]=3[NH:6][C:5]=2[CH2:4][CH2:3][NH:2]1.[CH2:22]=O.[BH4-].[Na+]>CO>[CH3:22][N:2]1[CH2:3][CH2:4][C:5]2[NH:6][C:7]3[C:8]([S:14][C:15]4[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=4)=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[CH2:1]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 68816513HCID 68816513, compound

Product 1

HCID 68817511HCID 68817511, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

4-Methylphenyl 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-yl sulfide (200 mg, 0.68 mmol) was brought to reflux with formaldehyde (37% aq., 0.68 mL) in MeOH (1.8 mL) for 30 minutes. The reaction was then cooled to 0° C. and sodium borohydride (89 mg, 1.3 mmol) was added slowly. The solution was allowed to stir at room temperature for 2 hours. Ice chips were then added and the reaction partitioned between CHCl3 and water. The aqueous layer was extracted with CHCl3 (3×10 mL). The combined extracts were washed with sat. NaCl (10 mL) and dried (MgSO4) and evaporated. The residue was dissolved in 1 mL EtOH and 1N HCl-Ether was added until no further precipitation was seen. The solid was filtered affording 2-methyl-6-[(4-methylphenyl)sulfanyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole as a light tan solid (178 mg, 76%). 1H NMR (CD3OD, 300 MHz) δ 7.49 (d, 1H, J=8.1 Hz), 7.26 (d, 1H, J=7.6 Hz), 7.07 (t, 1H, J=7.7 Hz), 6.97-7.02 (m, 4H), 4.42 (s, 2H), 3.58 (t, 2H, J=6.2 Hz), 3.05-3.21 (m, 5H), 2.25 (s, 3H) ppm.

Workup

  1. additionIce chips were then added
  2. customthe reaction partitioned between CHCl3 and water
  3. extractionThe aqueous layer was extracted with CHCl3 (3×10 mL)
  4. washThe combined extracts were washed with sat. NaCl (10 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. dissolutionThe residue was dissolved in 1 mL EtOH
  8. addition1N HCl-Ether was added until no further precipitation
  9. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-c0ea417047ee42ccbaca3dda57930bb3
Source dataset
uspto-grants-2009_09
Patent number
US07592454B2

Reaction notes

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