Methyl iodide → Ammonia

HRID 219043Notes

Reaction equation

HRID 219043 reaction equation
[CH3:1][N:2]([CH3:46])[C:3]1[CH:4]=[C:5]([CH:43]=[CH:44][CH:45]=1)[CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:28][C@@H:29]([C:31]1[CH:42]=[CH:41][C:34]2[O:35][C:36]([CH3:40])([CH3:39])[O:37][CH2:38][C:33]=2[CH:32]=1)[OH:30])[C:18](=[O:27])[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[I:47][CH3:48]>CN(C=O)C>[NH3:2].[I-:47].[CH3:40][C:36]1([CH3:39])[O:35][C:34]2[CH:41]=[CH:42][C:31]([C@@H:29]([OH:30])[CH2:28][N:17]([C:18](=[O:27])[O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][C:5]3[CH:4]=[C:3]([N+:2]([CH3:48])([CH3:1])[CH3:46])[CH:45]=[CH:44][CH:43]=3)=[CH:32][C:33]=2[CH2:38][O:37]1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 66845304HCID 66845304, compound

Product 2

HCID 222AmmoniaHCID 66845240HCID 66845240, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of benzyl 6-(2-{[3-(dimethylamino)benzyl]oxy}ethoxy)hexyl[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]carbamate (571 mg) in DMF (9 ml) was treated with iodomethane (0.09 ml) and the mixture was stirred 20° for 16 h. The solvent was evaporated in vacuo and the residue was purified by SPE (silica, 10 g). Elution with methanol-0.880 ammonia (19:1) gave the title compound (346 mg). LCMS RT=2.79 min.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by SPE (silica, 10 g)
  3. washElution with methanol-0

Sources & evidence

ORD record
ord-ab680097aca8488084fe96325b6600df
Source dataset
uspto-grants-2012_06
Patent number
US08198483B2

Reaction notes

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