Dimethylformamide dimethyl acetal → HCID 178483368, compound

HRID 76818Notes

Reaction equation

HRID 76818 reaction equation
[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[C:6]([O:10][C:11]([NH:13][CH2:14][C:15]1[C+:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]1[CH2:24][CH:25]=[C:26]([CH3:28])[CH:27]=[C:19]1[C:18]2([CH3:30])[CH3:29])=[O:12])([CH3:9])([CH3:8])[CH3:7].CO[CH:33](OC)[N:34]([CH3:36])[CH3:35].N12CCCN=C1CCCCC2>CN(C)C=O>[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[C:6]([O:10][C:11]([NH:13][CH2:14][C:15]1[C+:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]1[CH2:24][CH:25]=[C:26]([CH:28]=[CH:33][N:34]([CH3:36])[CH3:35])[CH:27]=[C:19]1[C:18]2([CH3:30])[CH3:29])=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178427980HCID 178427980, compound

Product 1

HCID 178483368HCID 178483368, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(tert-Butoxycarbonylamino-methyl)-8,10,10-trimethyl-10H-pyrido[1,2-a]indolylium perchlorate (34 g, 0.077 mol; Sigma-Aldrich) was placed in 1-L round-bottom, one-necked flask equipped with magnetic stir bar and a reflux condenser. 75 mL of dimethylformamide and 38.5 mL of 1,1-Dimethoxy-N,N-dimethylmethanamine (38.5 mL, 0.290 mol; Aldrich) were added to the flask followed by 1,8-Diazabicyclo[5.4.0]undec-7-ene (0.1 g, 0.0006 mol; Aldrich). The flask was immersed in oil bath with temperature set to 100° C. Stirring was started and continued for 30 min. The flask was cooled to room temperature, the solvent was evaporated in vacuum and the residue was recrystallized from methanol. The yield was 29 g (green crystals, 71% of theory).

Workup

  1. customone-necked flask equipped with magnetic stir bar and a reflux condenser
  2. customThe flask was immersed in oil bath with temperature
  3. customset to 100° C
  4. customthe solvent was evaporated in vacuum
  5. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-4b34c048141745f19091f47e5088fd7f
Source dataset
uspto-grants-2014_09
Patent number
US08835632B2

Reaction notes

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