Dimethylamine → HCID 19921658, compound

HRID 1647768Notes

Reaction equation

HRID 1647768 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:21][NH:22][CH3:23].[CH2:24]=O>C(O)C>[NH4+:1].[OH-:12].[CH3:21][N:22]([CH2:24][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:5]=2)[NH:1][CH:2]=1)[CH3:23]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 249092benzyl 1h-indol-5-ylcarbamate

Product 2

HCID 14923Ammonium HydroxideHCID 19921658HCID 19921658, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of phenylmethyl (1H-indol-5-yl)carbamate (3.76 g, 14.1 mmol) in ethanol (6 mL) was added dimethylamine (1.75 mL, 40% aq solution) and formaldehyde (1.25 mL, 40% aq solution). The reaction was heated at reflux for 16 h. The solvent was removed in vacuo and the residue treated with 10% Na2CO3 solution and extracted with four portions of ethyl acetate. The combined organic extracts were washed with saturated NaCl solution, dried with Na2CO3, filtered, and concentrated in vacuo. Silica gel chromatography (93:7:0.7 to 90:10:1 CH2Cl2 : MeOH:NH4OH gradient) of the concentrate afforded phenylmethyl [3-[(dimethylamino)methyl]-1H-indol-5-yl]carbamate (2.30 g, 51%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 16 h
  3. customThe solvent was removed in vacuo
  4. additionthe residue treated with 10% Na2CO3 solution
  5. extractionextracted with four portions of ethyl acetate
  6. washThe combined organic extracts were washed with saturated NaCl solution
  7. dry with materialdried with Na2CO3
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-db00517b79054215bcf17b34915240f3
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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