2-Chloro-1-methylpyridinium iodide → HCID 54059442, compound

HRID 978446Notes

Reaction equation

HRID 978446 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][C:8]=1[C:9]([OH:11])=O)=[O:5])[CH3:2].[I-].ClC1C=CC=C[N+]=1C.[F:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2([CH:45]3[CH2:50][CH2:49][N:48]([CH2:51][CH2:52][NH2:53])[CH2:47][CH2:46]3)[O:44][CH2:43][CH2:42][O:41]2)=[CH:36][CH:35]=1>O.ClCCl.C(N(CC)CC)C>[F:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2([CH:45]3[CH2:46][CH2:47][N:48]([CH2:51][CH2:52][NH:53][C:9]([C:8]4[CH:12]=[C:13]([O:16][CH2:17][C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)[CH:14]=[CH:15][C:7]=4[NH:6][C:4](=[O:5])[O:3][CH2:1][CH3:2])=[O:11])[CH2:49][CH2:50]3)[O:41][CH2:42][CH2:43][O:44]2)=[CH:36][CH:35]=1

Participants

7

Reactant 3

HCID 1670692-Chloro-1-methylpyridinium iodideHCID 12073663HCID 12073663, compoundHCID 14699815HCID 14699815, compound

Product 1

HCID 54059442HCID 54059442, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a stirred suspension of 19.6 parts of 2-[(ethoxycarbonyl)amino]-5-(phenylmethoxy)benzoic acid in 520 parts of dichloromethane were added 12.6 parts of N,N-diethylethanamine and the whole was stirred for 5 minutes. 15.9 Parts of 2-chloro-1-methylpyridinium iodide were added and stirring was continued for 90 minutes. A solution of 18.2 parts of 4-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-1-piperidineethanamine in 390 parts of dichloromethane was added dropwise to the whole. Upon completion, stirring was continued for 2.50 hours at room temperature. 150 Parts of water were added to the reaction mixture. The organic layer was separated, washed with a sodium hydrogen carbonate solution 10%, dried, filtered and evaporated. The oily residue was purified by HPLC over silica gel using a mixture of methylbenzene and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 24.7 parts (67%) of ethyl [2-[[2-[4[ 2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-1-piperidinyl]ethyl]aminocarbonyl]-4-(phenylmethoxy)phenyl]carbamate as a residue (25).

Workup

  1. stirringstirring
  2. waitwas continued for 90 minutes
  3. stirringUpon completion, stirring
  4. waitwas continued for 2.50 hours at room temperature
  5. customThe organic layer was separated
  6. washwashed with a sodium hydrogen carbonate solution 10%
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe oily residue was purified by HPLC over silica gel using
  11. additiona mixture of methylbenzene and methanol (95:5 by volume) as eluent
  12. customThe pure fractions were collected
  13. customthe eluent was evaporated

Sources & evidence

ORD record
ord-26eb53f3b242400b8f3567174c6b7908
Source dataset
uspto-grants-1987_05
Patent number
US04665075

Reaction notes

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