Triethylamine → N-(8-Methoxychroman-2-yl-methyl)-cyclohexanecarboxamide

HRID 129582Notes

Reaction equation

HRID 129582 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[C:6]([O:13][CH3:14])[CH:7]=[CH:8][CH:9]=2)[O:4]1.C(N(CC)CC)C.[CH:22]1([C:28](Cl)=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C(Cl)Cl>[CH3:14][O:13][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[O:4][CH:3]([CH2:2][NH:1][C:28]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:29])[CH2:12][CH2:11]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 15057554HCID 15057554, compound

Product 1

HCID 21843755N-(8-Methoxychroman-2-yl-methyl)-cyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 9.5 g (49 mmol) of 2-aminomethyl-8-methoxychroman and 4.9 ml (49 mmol) of triethylamine in 50 ml of anhydrous methylene chloride is added dropwise to a solution of 7.2 g (49 mmol) of cyclohexanecarbonyl chloride in 75 ml of anhydrous methylene chloride, while stirring and cooling with ice. After the mixture has been left to stand overnight, it is poured onto ice. Separation of the phases, extraction of the aqueous phase with methylene chloride, washing with saturated sodium chloride solution and drying of the combined organic phases over anhydrous sodium sulphate gives, after evaporation under a water pump vacuum, 14.5 g of crude amide, which is recrystallised from 160 ml of ethyl acetate. IR (KBr): 3307, 2931, 1642, 1485 and 1256 cm

Workup

  1. temperaturecooling with ice
  2. waitAfter the mixture has been left
  3. additionit is poured onto ice
  4. customSeparation of the phases, extraction of the aqueous phase with methylene chloride
  5. washwashing with saturated sodium chloride solution
  6. dry with materialdrying of the combined organic phases over anhydrous sodium sulphate
  7. customgives
  8. customafter evaporation under a water pump vacuum, 14.5 g of crude amide, which
  9. customis recrystallised from 160 ml of ethyl acetate

Sources & evidence

ORD record
ord-01eba354b94c477a9ed0d9fd67c46f0e
Source dataset
uspto-grants-1995_11
Patent number
US05468882

Reaction notes

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