Dibenzylamine → Tert-butyl 2-[(dibenzylamino)methyl]prop-2-enoate

HRID 1087975Notes

Reaction equation

[C:1]([O:5][C:6](=[O:11])[C:7]([CH2:9]Br)=[CH2:8])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:18]([NH:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(#N)C>[C:1]([O:5][C:6](=[O:11])[C:7]([CH2:9][N:25]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[CH2:8])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-(bromomethyl)propenoic acid t-butyl ester (20 g, 90.5 mmole) in dry acetonitrile (360 ml), cooled to 0° C., was treated with solid potassium carbonate (15.63 g, 113 mmole), followed by a solution of dibenzylamine (17.83 g, 90.5 mmole, in dry acetonitrile (600 ml), producing a 10° C. exotherm. The reaction was stirred at 0° C. for 0.5 hours, followed by 1 hour at room temperature, and then partitioned between water and diethyl ether. The ether phase was washed again with water, dried (sodium sulphate) and evaporated to yield the crude product (31 g) which was filtered through a pad of silica, eluting with hexane/CH2Cl2 (1:1), to yield 2-(dibenzylaminomethyl)propenoic acid t-butyl ester (23.8 g, 78%) as a solid, m.p. 62°-63° C. Found C,78.09; H,8.20; N,4.18. C22H27NO2 requires C,78.3; N,8.06; N,4.15 %.

Workup

waitfollowed by 1 hour at room temperature
custompartitioned between water and diethyl ether
washThe ether phase was washed again with water
dry with materialdried (sodium sulphate)
customevaporated
customto yield the crude product (31 g) which
filtrationwas filtered through a pad of silica
washeluting with hexane/CH2Cl2 (1:1)

Sources & evidence

ORD record: ord-5f8c617f47e940dcb052464c57546eac
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04960792

Reaction notes

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