Hydrochloric Acid → HCID 9899243, compound

HRID 1582440Notes

Reaction equation

HRID 1582440 reaction equation
[CH:1]([C:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]2[CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][CH2:16][C:4]=12)=[O:2].Cl>CO>[CH2:16]1[C:4]2=[C:3]([CH:1]=[O:2])[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]2[CH2:12][CH2:13][NH:14][CH2:15]1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 22720322HCID 22720322, compound

Product 1

HCID 9899243HCID 9899243, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of tert-butyl 11-formyl-1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indole-3-carboxylate (225 mg, 0.72 mmol) in methanol (5 mL) is cooled to 0° C. and treated with a solution of saturated hydrochloric acid in methanol (3 mL). After 15 min, the yellow homogenous solution is treated with an additional portion of the hydrochloric acid solution and warmed to rt. After 1 hr, the reaction is concentrated under reduced pressure, diluted with 2M sodium hydroxide (15 mL), and extracted twice with dichloromethane (20 mL). The combined organics are washed once with brine (20 mL), dried over MgSO4, filtered, and concentrated to give 165 mg of a crude solid. This material is purified by LC (230-400) silica gel eluting with 10% methanol/dichloromethane to afford 118 mg of 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole-11-carbaldehyde as an off-white solid. This material is recrystallized form ethyl acetate/heptane to give a light yellow solid, mp 167-168° C. IR (drift) 3307, 2941, 1636, 1464, 1429, 1391, 1367, 1350, 1269, 1205, 1124, 1052, 775, 750, 731 cm−1.

Workup

  1. temperaturewarmed to rt
  2. waitAfter 1 hr
  3. concentrationthe reaction is concentrated under reduced pressure
  4. additiondiluted with 2M sodium hydroxide (15 mL)
  5. extractionextracted twice with dichloromethane (20 mL)
  6. washThe combined organics are washed once with brine (20 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give 165 mg of a crude solid
  11. customThis material is purified by LC (230-400) silica gel eluting with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-06272fa294e94bf389ec9dcc44c73176
Source dataset
uspto-grants-2004_05
Patent number
US06734301B2

Reaction notes

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