Dibutylamine → HCID 53779816, compound

HRID 400201Notes

Reaction equation

HRID 400201 reaction equation
[CH2:1]([NH:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].C([Al](CC)CC)C.[CH:17]12[O:23][CH:22]1[CH2:21][CH2:20][CH2:19][CH2:18]2.[OH-].[Na+]>ClCCl.CCCCCC>[CH2:1]([N:5]([C@@H:21]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:22]1[OH:23])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 8148DibutylamineHCID 9246Cyclohexene oxideHCID 14798Sodium HydroxideHCID 16682930Triethylaluminum

Product 1

HCID 53779816HCID 53779816, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

A! A solution of 43 ml (0.25 mole) of dibutylamine in 770 ml of dichloromethane was added with a 0.91M solution of 280 ml (0.025 mole) of triethyl-aluminium in hexane, at 0° C. under argo, and the resultant reaction mixture was stirred for 30 minutes at room temperature, then dropwise added with 25.8 ml (0.25 mole) of 7-oxabicyclo[4.1.0]heptane, and stirred overnight. A 6M solution of 200 ml (1.2 moles) of sodium hydroxide was added very slowly, and the mixture was stirred for 2 hours at room temperature. The phases were separated, and the organic one was washed with water (2×50 ml), anhydrified over sodium sulfate and evaporated. The resultant crude was distilled under vacuum to provide 43.7 g (yield: 75%) of trans-2-(N,N-dibutylamino)-cyclohexanol (b.p.--105°-107° C./1 mmHg).

Workup

  1. customthe resultant reaction mixture
  2. stirringstirred overnight
  3. stirringthe mixture was stirred for 2 hours at room temperature
  4. customThe phases were separated
  5. washthe organic one was washed with water (2×50 ml)
  6. customover sodium sulfate and evaporated
  7. distillationThe resultant crude was distilled under vacuum

Sources & evidence

ORD record
ord-2b6d200ff520422486781bb1f1d7cd72
Source dataset
uspto-grants-1998_10
Patent number
US05827881

Reaction notes

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