Trifluoroacetic acid → [4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-methyl-amine

HRID 1841608Notes

Reaction equation

HRID 1841608 reaction equation
C(O[C:6](=O)[N:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])=[CH:11][CH:10]=1)C)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:22][N:20]([CH3:21])[CH2:19][CH2:18][CH2:17][C:16]#[C:15][C:12]1[CH:11]=[CH:10][C:9]([NH:7][CH3:6])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68614538[4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 23446691[4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-methyl-amineYield 106%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.45 g (4.58 mmol) of [4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-methyl-carbamic acid tert-butyl ester in 25 ml CH2Cl2 was treated at 0° C. with 11.5 ml TFA (during 20 min) and warmed up to room temperature during 1 h. The solution was concentrated and the residual oil was extracted with aqueous sat. NaHCO3 (+Na2CO3)/EtOAc (3×). The organic phase was dried (Na2SO4) and evaporated to yield 1.05 g (quantitative) of [4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-methyl-amine MS: 217 (MH+).

Workup

  1. concentrationThe solution was concentrated
  2. extractionthe residual oil was extracted with aqueous sat. NaHCO3 (+Na2CO3)/EtOAc (3×)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-d707626f412842688f2e2474fa0128f3
Source dataset
uspto-grants-2004_01
Patent number
US06683201B2

Reaction notes

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