Hydrochloric Acid → HCID 15456878, compound

HRID 1005498Notes

Reaction equation

HRID 1005498 reaction equation
[F:1][C:2]([F:33])([C:23]([F:32])([F:31])[C:24]([F:30])([F:29])[C:25]([F:28])([F:27])[F:26])[CH2:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][CH2:9][C:10]([F:22])([F:21])[C:11]([F:20])([F:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14].[CH2:34]=O.Cl>C(O)=O>[F:1][C:2]([F:33])([C:23]([F:31])([F:32])[C:24]([F:29])([F:30])[C:25]([F:26])([F:27])[F:28])[CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH2:9][C:10]([F:21])([F:22])[C:11]([F:19])([F:20])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])[CH3:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 18792138HCID 18792138, compound

Product 1

HCID 15456878HCID 15456878, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A solution of bis(4,4,5,5,6,6,7,7,7-nonafluoroheptyl)amine (3.0 g) and formic acid (90%, 1.5 g) was cooled in an ice-water bath and 8 ml of formaldehyde (37% weight) was added. The solution was slowly heated to 90° C. and maintained overnight. (Foaming and gas evolution at 60-75° C.) Concentrated hydrochloric acid (1 ml) was added and 7 ml of solution were removed by distillation. The remaining solution was cooled and treated with KOH (aq. 10%) to pH 11. The mixture was extracted with methylene chloride (3×50 ml). The combined methylene chloride extracts were washed with water (2×50 ml), dried over sodium sulfate, and concentrated on vacuum to give a residue. Distillation of the residue at reduced pressure gave 2.7 g of bis(4,4,5,5,6,6,7,7,7-nonafluoroheptyl)methylamine, yield 88%. 19F NMR (CDCl3) -81.7 (m, 6F), -115.1 (m, 4F), -125.1 (m, 4F), -126.6 (m, 4F) ppm. 1H NMR (CDCl3) 2.40 (t, J=6 Hz, 4H), 2.19 (s, 3H), 2.16 (m, 4H), 1.76 (m, 4H) ppm. 13C NMR (CDCl3) 18.4, 28.7 (t, J=23 Hz), 41.3, 56.5, 108-123 (m) ppm. MS (m/e) 532 (M+ -F, 7.5%), 382 (1.0%), 304 (100%), 195 (0.6%), 169 (0.8%), 119 (2.5%), 69 (9.4%).

Workup

  1. temperaturemaintained overnight
  2. custom7 ml of solution were removed by distillation
  3. temperatureThe remaining solution was cooled
  4. additiontreated with KOH (aq. 10%) to pH 11
  5. extractionThe mixture was extracted with methylene chloride (3×50 ml)
  6. washThe combined methylene chloride extracts were washed with water (2×50 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated on vacuum
  9. customto give a residue
  10. distillationDistillation of the residue at reduced pressure

Sources & evidence

ORD record
ord-1bc6d90d0c6a4864a9c757d1f454024c
Source dataset
uspto-grants-2000_04
Patent number
US06054615

Reaction notes

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