Benzhydrylamine → HCID 57753282, compound

HRID 225673Notes

Reaction equation

[F:1][C:2]1[C:13]([I:14])=[CH:12][C:5]([CH2:6]OS(C)(=O)=O)=[C:4]([CH2:15]OS(C)(=O)=O)[CH:3]=1.C(N(CC)C(C)C)(C)C.[C:30]1([CH:36]([NH2:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C=O)C>[CH:36]([N:43]1[CH2:15][C:4]2[C:5](=[CH:12][C:13]([I:14])=[C:2]([F:1])[CH:3]=2)[CH2:6]1)([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 5.93 mmol methanesulfonic acid 4-fluoro-5-iodo-2-methanesulfonyloxymethyl-benzyl ester and 14.8 mmol N,N-diisopropylethylamine in 7 ml DMF at 0° C. was added dropwise a solution of 6.53 mmol diphenylmethylamine in 5 ml DMF. The mixture was heated at 60° C. for 16 h and was then cooled to room temperature and partitioned between ethyl acetate and water. The organic phase was washed sequentially with water and brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by chromatography on silica gel (eluant: ethyl acetate/heptane) to afford the title compound as a light yellow solid (55% yield).

Workup

temperaturewas then cooled to room temperature
custompartitioned between ethyl acetate and water
washThe organic phase was washed sequentially with water and brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by chromatography on silica gel (eluant: ethyl acetate/heptane)

Sources & evidence

ORD record: ord-65d2e6a29b844812a90a65c83445e2d3
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557114B2

Reaction notes

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