Potassium Hydroxide → HCID 67305957, compound

HRID 1921970Notes

Reaction equation

HRID 1921970 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[CH:6]=[C:5]([C:15](=[O:17])[CH3:16])[CH:4]=1.Cl.Cl[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]Cl.C(N(C(C)C)CC)(C)C.[OH-].[K+]>O.C1(C)C=CC=CC=1>[CH3:14][O:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([C:15](=[O:17])[CH3:16])[CH:4]=[C:3]2[N:2]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 81531DiisopropylethylamineHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 67305368HCID 67305368, compound

Product 1

HCID 67305957HCID 67305957, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

1-(4-amino-6-methoxynaphthalen-2-yl)ethanone hydrochloride (3) (3.0 g) and bis(2-chloroethyl)amine hydrochloride (2.54 g) were charged in a flask and to them was added toluene (100 ml) and diisopropylethylamine (6.5 ml). The reaction was heated to 120° C. and allowed to stir overnight. Upon completion, 5 N aqueous potassium hydroxide (50 ml) and water (100 ml) were added and the reaction was allowed to stir for 2 hours at room temperature. The liquids were decanted and to them was added concentrated hydrochloric acid until the aqueous was made acidic. 1-(6-methoxy-4-(piperazin-1-yl)naphthalen-2-yl)ethanone (106) was an orange-brown solid that was filtered and used with no further purification (3.5 g) LCMS (m/z): 285 [M+H].

Workup

  1. stirringto stir for 2 hours at room temperature
  2. customThe liquids were decanted and to them
  3. additionwas added concentrated hydrochloric acid until the
  4. filtrationwas filtered
  5. customused with no further purification (3.5 g) LCMS (m/z)

Sources & evidence

ORD record
ord-055af3aa6b4843cc8fd7c3ddb302527d
Source dataset
uspto-grants-2012_05
Patent number
US08173808B2

Reaction notes

Loading…