4-Chlorophenyl chloroformate → [4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-methyl-carbamic acid 4-chloro-phenyl ester

HRID 1841609Notes

Reaction equation

HRID 1841609 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][CH2:5][C:6]#[C:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH3:15])=[CH:10][CH:9]=1.[CH:17]1[C:22]([O:23][C:24](Cl)=[O:25])=[CH:21][CH:20]=[C:19]([Cl:27])[CH:18]=1>O1CCOCC1.C([O-])(O)=O.[Na+]>[Cl:27][C:19]1[CH:20]=[CH:21][C:22]([O:23][C:24](=[O:25])[N:14]([C:11]2[CH:12]=[CH:13][C:8]([C:7]#[C:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:16])[CH3:1])=[CH:9][CH:10]=2)[CH3:15])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 1390594-Chlorophenyl chloroformateHCID 23446691[4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-methyl-amine

Product 1

HCID 9969421[4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-methyl-carbamic acid 4-chloro-phenyl esterYield 54.9%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 59 mg (0.27 mmol) of [4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-methyl-amine in 0.3 ml dioxane was treated with 0.07 ml (0.55 mmol; 2 equivalents) Hünigsbase and dropwise with a solution of 0.05 ml (0.27 mmol) 4-chlorophenylchloroformate in 0.45 ml dioxane. The mixture was then immediately dissolved in aqueous saturated NaHCO3 IEt2O (3×). The organic phase was dried over Na2SO4 and evaporated. Flash column chromatography on silica gel with CH2Cl2/MeOH (95:5) yielded 55 mg (54%) of [4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-methyl-carbamic acid 4-chloro-phenyl ester, MS: 371 (MH+, 1Cl).

Workup

  1. dry with materialThe organic phase was dried over Na2SO4
  2. customevaporated

Sources & evidence

ORD record
ord-8486033ed4dc49d1bf9768fe3910d639
Source dataset
uspto-grants-2004_01
Patent number
US06683201B2

Reaction notes

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