1,5-Dibromopentane → HCID 21407936, compound

HRID 2072361Notes

Reaction equation

HRID 2072361 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][Br:7].C([O:10][C:11](=[O:29])[CH:12]([O:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[O:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)C.C(OC(=O)C(Br)OC1C=CC(Cl)=CC=1)C.ClC1C=CC(OC(OC2C=CC([N+]([O-])=O)=CC=2)C(O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>C(O)CCC>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][Br:7])=[CH:16][CH:15]=2)[C:11]([OH:29])=[O:10])=[CH:23][CH:24]=1

Participants

7

Reactant 5

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 12376161Ethyl bromo(4-chlorophenoxy)acetateHCID 21407938HCID 21407938, compoundHCID 57241026HCID 57241026, compound

Product 1

HCID 21407936HCID 21407936, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2.3 g. of 1,5-dibromopentane, 3.2 g. of (4-chlorophenoxy)-(4-aminophenoxy)-acetic acid ethyl ester [obtainable by reacting Na-4-nitrophenolate with α-bromo-α-(4-chlorophenoxy)-acetic acid ethyl ester to obain the ethyl ester of (4-chlorophenoxy)-(4-nitrophenoxy)-acetic acid and subsequent hydrogenation], and 1.4 g. of K2CO3 are refluxed for 12 hours in 40 ml. of n-butanol. As an intermediate compound, the ethyl ester of (4-chlorophenoxy)-[4-(5-bromopentylamino)-phenoxy]-acetic acid is produced. After working up the mixture as usual, (4-chlorohenoxy)-(4-piperidinophenoxy)-acetic acid ethyl ester is obtained.

Sources & evidence

ORD record
ord-60bee018ddd545439c9c7c075783bad3
Source dataset
uspto-grants-1977_09
Patent number
US04051170

Reaction notes

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