Hydrochloric Acid → n,n-Dimethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]butylamine hydrochloride

HRID 1194447Notes

Reaction equation

HRID 1194447 reaction equation
[CH:1]([NH:3][CH:4]([C:8]1([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[CH2:11][CH2:10][CH2:9]1)[CH2:5][CH2:6][CH3:7])=O.Cl.[OH-].[Na+].[CH2:23]=O>CC(O)C.C(O)=O.O.CCOCC>[ClH:18].[CH3:1][N:3]([CH:4]([C:8]1([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[CH2:11][CH2:10][CH2:9]1)[CH2:5][CH2:6][CH3:7])[CH3:23]

Participants

9

Reactant 4

HCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 13083182N-formyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]butylamine

Product 1

HCID 13083291n,n-Dimethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]butylamine hydrochloride

Reagents, catalysts & solvents 4

HCID 284Formic AcidSolventHCID 962WaterSolvent3×HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

The product of Example 7 (8.3 g), diethyleneglycoldimethyl ether (50 ml), water (20 ml) and concentrated hydrochloric acid (20 ml) were mixed and heated under reflux for sixteen hours. The mixture was poured into water, aqueous NaOH was added and the product extracted into ether. Evaporation gave a dark oil. A sample of this oil (7.9 g), water (0.7 ml) and formic acid (6.5 ml) were mixed and formaldehyde (6.5 m) added. The mixture was heated under reflux for three hours and then concentrated hydrochloric acid (10 ml) and propan-2-ol (10 ml) were added. Evaporation to dryness gave N,N-dimethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]butylamine hydrochloride (m.p. 195°-196°) as a white solid (Formula I R1 =propyl; R2 =H; R3, R4 =Me; R5 =4-Cl and R6 =3-Cl).

Workup

  1. temperatureheated
  2. temperatureunder reflux for sixteen hours
  3. additionwas added
  4. extractionthe product extracted into ether
  5. customEvaporation
  6. customgave a dark oil
  7. temperatureThe mixture was heated
  8. temperatureunder reflux for three hours
  9. customEvaporation to dryness

Sources & evidence

ORD record
ord-dfaa02d2c95349ee92488eee3cc18cf8
Source dataset
uspto-grants-1989_03
Patent number
US04814352

Reaction notes

Loading…