Styrene → 1-(3-Phenylprop-2-en-1-yl)pyrrolidine

HRID 890345Notes

Reaction equation

HRID 890345 reaction equation
[N:1]1([CH2:6][CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:15]([CH:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=C.[CH2:25]=[CH:26][C:27]1C=CC=C[CH:28]=1.N1(CC2C=CC(C=C)=CC=2)CCCC1.[N:47]1([CH2:52][C:53]2[CH:54]=[C:55]([CH:58]=[CH:59][CH:60]=2)[CH:56]=[CH2:57])[CH2:51][CH2:50][CH2:49][CH2:48]1.CN(CCN(C)C)C.[Li]CCCC>>[N:1]1([CH2:6][CH:7]=[CH:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:15]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:25]=[CH:26][CH:27]=[CH2:28].[N:47]1([CH2:52][CH:53]=[CH:54][C:55]2[CH:56]=[CH:57][CH:60]=[CH:59][CH:58]=2)[CH2:48][CH2:49][CH2:50][CH2:51]1

Participants

9

Reactant 7

HCID 7501StyreneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-HCID 120951841-[(4-ethenylphenyl)methyl]-pyrrolidine2×HCID 22149529HCID 22149529, compoundHCID 667438361-(3-Phenylprop-2-en-1-yl)pyrrolidineHCID 178418339Butyllithium

Product 2

HCID 667438361-(3-Phenylprop-2-en-1-yl)pyrrolidineHCID 131725271HCID 131725271, compound

Procedure

In this example, a Feb. 18, 1980 pyrrolidinomethylstyrene/styrene/1,3-butadiene terpolymer was prepared using the procedures described in Example 34 except that pyrrolidinomethyl styrene (PMS) was used instead of PES. The PMS was prepared from vinylbenzylchloride and normally was a mixture 3-pyrrolidino methyl) styrene and 4-(pyrrolidino methyl) styrene. The molar ratio of 3-(pyrrolidinomethyl) styrene to 4-(pyrrolidino methyl) styrene was normally closed to 60:40. Also, 0.55 ml of a neat TMEDA and 2.1 ml of 1.6 M n-BuLi were used as the initiator.

Sources & evidence

ORD record
ord-fc63eaba7f8c44abbeff8a6bc07b17e3
Source dataset
uspto-grants-2006_02
Patent number
US06995224B2

Reaction notes

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