1-Butanol → HCID 178441836, compound

HRID 1940190Notes

Reaction equation

HRID 1940190 reaction equation
[C:1]([C:3]1([NH:8][C:9](=O)[CH2:10][CH2:11][CH2:12][CH3:13])[CH2:7][CH2:6][CH2:5][CH2:4]1)#[N:2].[ClH:15].C([OH:20])CCC>>[ClH:15].[CH2:10]([C:9]1[NH:8][C:3]2([CH2:7][CH2:6][CH2:5][CH2:4]2)[C:1](=[O:20])[N:2]=1)[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 3

HCID 2631-Butanol2×HCID 313Hydrochloric AcidHCID 11790092N-(1-Cyanocyclopentyl)pentanamide

Product 1

HCID 178441836HCID 178441836, compound

Conditions

Temperature
115 °C

Procedure

6.88 g (30 mmol) of N-(1-cyanocyclopentyl)pentanamide (content 84.7 percent), 16.66 g of dried butanol and 10.06 g (39 mmol) of a freshly-prepared 14.13 percent solution of hydrogen chloride in butanol were heated to the reflux point (preheated oil bath) under nitrogen, with stirring, and product precipitated out as soon as the internal temperature reached ca. 100° C. After 2.9 hours of reflux (115° C.), the mixture was cooled to 1° C. and left to stand for 1 hour at this temperature. The product which had precipitated out was filtered off, washed with 10 ml of ice-cold butanol and dried at 40° C./24 mbar. The yield of the product was 4.93 g (66 percent), content 92.7 percent (HPLC).

Workup

  1. customproduct precipitated out as soon as the internal temperature
  2. customreached ca. 100° C
  3. temperaturethe mixture was cooled to 1° C.
  4. waitleft
  5. customThe product which had precipitated out
  6. filtrationwas filtered off
  7. washwashed with 10 ml of ice-cold butanol
  8. customdried at 40° C./24 mbar

Sources & evidence

ORD record
ord-a37e1890564644f399a1926adaceb973
Source dataset
uspto-grants-1997_12
Patent number
US05698704

Reaction notes

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