Formaldehyde → HCID 9920667, compound

HRID 1582444Notes

Reaction equation

HRID 1582444 reaction equation
[CH2:1]1[C:7]2=[CH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[N:6]2[CH2:5][CH2:4][NH:3][CH2:2]1.C=O.[C:17]([BH3-])#N.[Na+]>CO>[CH3:17][N:3]1[CH2:2][CH2:1][C:7]2=[CH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[N:6]2[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 97940922,3,4,5-Tetrahydro-1H-[1,4]diazepino[1,7-a]indole

Product 1

HCID 9920667HCID 9920667, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole (372 mg, 2.0 mmol) in methanol (25 mL) is treated with a solution of 37% aqueous formaldehyde (24 mmol, 2.0 mL). The resulting clear solution is treated with a single portion of sodium cyanoborohydride (251 mg, 4.0 mmol) turning slightly a lighter yellow color. After 40 min, the reaction is quenched with 1M hydrochloric acid (15 mL), stirred over 10 min, basified to pH 13, volatiles removed under reduced pressure, and extracted twice with ethyl acetate (25 mL). The combined organics are washed with brine (20 mL), dried over MgSO4, filtered, and concentrated to give a crude oil. This material is purified by LC (230-400 silica gel) eluting with 70% acetone/heptane to afford 234 mg (58%) of 3-methyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole as a white solid, mp 59-60° C. IR (drift) 2924, 2781, 2758, 2741, 1458, 1413, 1377, 1339, 1326, 1315, 1290, 1133, 1003, 799, 737 cm−1. MS (EI) m/z 200 (M+).

Workup

  1. customthe reaction is quenched with 1M hydrochloric acid (15 mL)
  2. customvolatiles removed under reduced pressure
  3. extractionextracted twice with ethyl acetate (25 mL)
  4. washThe combined organics are washed with brine (20 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude oil
  9. customThis material is purified by LC (230-400 silica gel)
  10. washeluting with 70% acetone/heptane

Sources & evidence

ORD record
ord-47834f3d8c224f1db2d0db372fe61fb6
Source dataset
uspto-grants-2004_05
Patent number
US06734301B2

Reaction notes

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