Hydrochloric Acid → Benzophenone hydrochloride

HRID 249273

Reaction equation

HRID 249273 reaction equation
CN(C)CCCCCCO.O[C:12]1[CH:25]=[CH:24][C:15]([C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[ClH:57]>O1CCCC1.CCOCC>[ClH:57].[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])[C:15]1[CH:24]=[CH:25][CH:12]=[CH:13][CH:14]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 143474-HydroxybenzophenoneHCID 746236-Dimethylaminohexan-1-olHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 19775659Benzophenone hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 2.5 g of N,N-dimethyl-6-amino-1-hexanol (Bull. Soc. Chim. France 1975, 2315), 3.4 g of 4-hydroxybenzophenone (Beilstein 8 (III), 1263), 4.5 g of triphenylphosphine and 140 ml of tetrahydrofuran was treated slowly at 20° with a solution of 2.7 ml of diethyl azodicarboxylate in 15 ml of tetrahydrofuran. After the dropwise addition the mixture was stirred at room temperature for a further 1 hour. The reaction mixture was evaporated in a rotary evaporator and the residue was chromatographed on 400 g of neutral aluminium oxide (activity grade III) with hexane:ethyl acetate (7:3). The yellowish oil obtained was dissolved in 25 ml of ether, whereupon the solution was treated with 25 ml of a 10 percent solution of hydrogen chloride in ether. The colorless crystals which separate were filtered off under suction, washed with ether and recrystallized from acetone. There were obtained 1.93 g (31%) of 4-[(6-dimethylamino)hexyl)oxy]benzophenone hydrochloride of m.p. 121°.

Workup

  1. additionAfter the dropwise addition the mixture
  2. customThe reaction mixture was evaporated in a rotary evaporator
  3. customthe residue was chromatographed on 400 g of neutral aluminium oxide (activity grade III) with hexane:ethyl acetate (7:3)
  4. customThe yellowish oil obtained
  5. customThe colorless crystals which separate
  6. filtrationwere filtered off under suction
  7. washwashed with ether
  8. customrecrystallized from acetone

Sources & evidence

ORD record
ord-41df85ac0239484fb58d77371c74847d
Source dataset
uspto-grants-1993_05
Patent number
US05214046

Linked notes

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