Methanol → HCID 69783903, compound

HRID 1063377Notes

Reaction equation

HRID 1063377 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]#[C:18][CH2:19][CH2:20][CH2:21]I)[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.C[CH:24]=[CH:25][CH2:26][NH2:27].[CH3:28]O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]#[C:18][CH2:19][CH2:20][CH2:21][N:27]([CH2:26][CH:25]=[CH2:24])[CH3:28])[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 304472-Buten-1-amineHCID 69784064HCID 69784064, compound

Product 1

HCID 69783903HCID 69783903, compoundYield 44%

Procedure

300 mg (corresponds to 0.7 mmol) of crude 4-(5-Iodo-pent-1-ynyl)-piperidine-1-carboxylic acid 4-chloro-phenyl ester in 5 ml MeOH was treated with 0.7 ml (6.95 mmol) of N-methylallylamine (at 0° C.). The reaction was stirred overnight at room temperature and partitioned between aqueous 1N NaOH /ether (3×), the organic phases were dried (Na2SO4) and evaporated. Purification by flash-chromatography on silica gel (CH2Cl2/MeOH 19:1) gave 116 mg (44% over two steps) of 4-[5-(Allyl-methyl-amino)-pent-1-ynyl]-piperidine-1-carboxylic acid 4-chloro-phenyl ester, MS: 375 (MH+, 1Cl).

Workup

  1. custompartitioned between aqueous 1N NaOH /ether (3×)
  2. dry with materialthe organic phases were dried (Na2SO4)
  3. customevaporated
  4. customPurification by flash-chromatography on silica gel (CH2Cl2/MeOH 19:1)

Sources & evidence

ORD record
ord-a789a9b4e1094345aec72906684adafc
Source dataset
uspto-grants-2005_11
Patent number
US06964974B2

Reaction notes

Loading…