N,N-Dimethyl-1,3-propanediamine → N-(3-(Dimethylamino)propyl) perfluorohexane sulfonamide

HRID 1885400Notes

Reaction equation

HRID 1885400 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][NH2:7])[CH3:3].C(N(CC)CC)C.[F:15][C:16]([F:37])([S:33](F)(=[O:35])=[O:34])[C:17]([F:32])([F:31])[C:18]([F:30])([F:29])[C:19]([F:28])([F:27])[C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22]>C1(C)C=CC=CC=1>[C:16]([S:33]([NH:7][CH2:6][CH2:5][CH2:4][N:2]([CH3:3])[CH3:1])(=[O:35])=[O:34])([C:17]([C:18]([C:19]([C:20]([C:21]([F:23])([F:24])[F:22])([F:25])[F:26])([F:28])[F:27])([F:30])[F:29])([F:32])[F:31])([F:37])[F:15]

Participants

5

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamine2×HCID 8471Triethylamine2×HCID 679181-Hexanesulfonyl fluoride, 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluoro-2×

Product 1

HCID 111913N-(3-(Dimethylamino)propyl) perfluorohexane sulfonamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of dimethylaminopropylamine, H2NC3H6N(CH3)2 (12.2 g, 0.12 mole), triethylamine, (C2H5)3N (8.1 g, 0.08 mole) and toluene (60 g) was first prepared at ambient temperature and about atmospheric pressure in an inert atmosphere of nitrogen. To this mixture was added perfluorohexanesulfonyl fluoride, C6F13SO2F (41.0 g, 0.10 mole). The total mixture was then heated in a stainless steel reaction vessel at 90° C. for a period of about 3 hours forming a homogeneous reactant solution. During this period the aforementioned Reaction (a) takes place to produce intermediate N-[3-(N',N'-dimethylamino)propyl]perfluorohexane sulfonamide, C6F13SO2N(H)C3H6N(CH3)2.

Workup

  1. customwas first prepared at ambient temperature
  2. customforming a homogeneous reactant solution

Sources & evidence

ORD record
ord-c5c6fb5456d54334ac88f1b7cd480729
Source dataset
uspto-grants-1992_09
Patent number
US05144069

Reaction notes

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