Benzylamine → HCID 54426674, compound

HRID 865613Notes

Reaction equation

[O:1]1[CH2:20][CH:2]1[CH2:3][O:4][CH2:5][CH2:6][CH2:7][Si:8]([CH3:19])([O:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[O:9][Si:10]([CH3:13])([CH3:12])[CH3:11].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)(C)C>[CH2:21]([NH:28][CH2:20][CH:2]([OH:1])[CH2:3][O:4][CH2:5][CH2:6][CH2:7][Si:8]([CH3:19])([O:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[O:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A 500-ml, three-necked, round-bottomed flask equipped with a stirrer, addition funnel, and condenser was charged with 100 g (0.30 mole) of the epoxy trisiloxane (Compound I) of Example 1 dissolved in 200 ml of isopropanol. The addition funnel was charged with a solution of 42.8 g (0.4 mole) of benzylamine (Aldrich) in 100 ml of isopropanol; the solution was added drop-wise to the flask contents at room temperature. The resulting reaction solution was heated at 80° C. for eight hours, after which time the solvent was removed under reduced pressure using a rotary evaporator. The residue, an oil, was passed through a short silica column using 10% ethyl acetate in hexane as eluent. The yield of Compound V, a colorless oil, was 127.8 g (97%). The following elemental analysis was obtained:

Workup

customA 500-ml, three-necked, round-bottomed flask equipped with a stirrer, addition funnel, and condenser
additionthe solution was added drop-wise to the flask contents at room temperature
customThe resulting reaction solution
customafter which time the solvent was removed under reduced pressure
customa rotary evaporator
customThe following elemental analysis was obtained

Sources & evidence

ORD record: ord-421cfe939bc84f5cb7eb371e11a63fce
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05567372

Reaction notes

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