Triethylamine → 2-Phenyl-5-cyclopropylcarbonyl-4,6,7,8-tetrahydrofuro[3,2-c]azepine

HRID 1606181Notes

Reaction equation

HRID 1606181 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[C:7]1([C:13]2[O:22][C:21]3[CH2:20][CH2:19][CH2:18][NH:17][CH2:16][C:15]=3[CH:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:7]1([C:13]2[O:22][C:21]3[CH2:20][CH2:19][CH2:18][N:17]([C:4]([CH:1]4[CH2:3][CH2:2]4)=[O:5])[CH2:16][C:15]=3[CH:14]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 215460862-Phenyl-4,6,7,8-tetrahydrofuro[3,2-c]azepine

Product 1

HCID 215460762-Phenyl-5-cyclopropylcarbonyl-4,6,7,8-tetrahydrofuro[3,2-c]azepine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 1.8 g. of cyclopropylcarbonyl chloride in 50 ml. of dry chloroform is added dropwise to a cooled mixture of 3.1 g. of 2-phenyl-4,6,7,8-tetrahydrofuro[3,2-c]azepine and 1.7 g. of triethylamine in 50 ml. of dry chloroform. After addition, the reaction mixture is stirred at ambient temperature for 20 hours, washed with water and dried. The chloroform is removed and the residue is triturated with n-hexane to produce a solid product. The product is recrystallized from n-hexane to give 2-phenyl-5-cyclopropylcarbonyl-4,6,7,8-tetrahydrofuro[3,2-c]azepine, m.p. 108°-110°C.

Workup

  1. additionAfter addition
  2. washwashed with water
  3. customdried
  4. customThe chloroform is removed
  5. customthe residue is triturated with n-hexane
  6. customto produce a solid product
  7. customThe product is recrystallized from n-hexane

Sources & evidence

ORD record
ord-8930b3f462814145b10615bef1f1da66
Source dataset
uspto-grants-1976_04
Patent number
US03952025

Reaction notes

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