Diethylene Glycol Monoethyl Ether → 2-[4-(5-Carbamoyl-3-indolyl)butyl]-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine

HRID 621579Notes

Reaction equation

HRID 621579 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][C:19]2[C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[O:24][C:18]=2[CH2:17]1)#[N:2].[OH-].[Na+].C([O:33]CCOCCO)C>O>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][C:19]2[C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[O:24][C:18]=2[CH2:17]1)(=[O:33])[NH2:2]

Participants

5

Reactant 3

HCID 8146Diethylene Glycol Monoethyl EtherHCID 14798Sodium HydroxideHCID 212433352-[4-(5-Cyano-3-indolyl)butyl]-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine

Product 1

HCID 212432852-[4-(5-Carbamoyl-3-indolyl)butyl]-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 36.9 g of 2-[4-(5-cyano-3-indolyl)butyl]-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine (obtainable from the corresponding 5-formyl compound via the oxime), 27.1 g of NaOH, 520 ml of water and 420 ml of diethylene glycol monoethyl ether is stirred at a bath temperature of 140° for 3 hours. The mixture is cooled, the usual working up is carried out, and 2-[4-(5-carbamoyl-3-indolyl)butyl]-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridine is obtained.

Workup

  1. temperatureThe mixture is cooled

Sources & evidence

ORD record
ord-82a37eaa98bd48478e050945bbbd9fb6
Source dataset
uspto-grants-1989_04
Patent number
US04824852

Reaction notes

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