Benzyl Chloride → HCID 23337738, compound

HRID 903136Notes

Reaction equation

HRID 903136 reaction equation
[CH3:1][C:2]1([CH3:15])[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3.[H-].[Na+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[C:19]1([CH2:18][N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]3[CH2:5][CH2:4][O:3][C:2]([CH3:15])([CH3:1])[C:7]2=3)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 12230454HCID 12230454, compound

Product 1

HCID 23337738HCID 23337738, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,3,4,9-Tetrahydro-1,1-dimethylpyrano[3,4-b]indole (5 g, 25 mmole, described by C. A. Demerson et al., cited above) was added portionwise to a suspension of sodium hydride (3 g, 58% dispersion in mineral oil) in 25 ml of dry dimethylformamide. This was stirred at room temperature for one hour. Benzyl chloride (3.8 g, 30 mmole) was added dropwise with ice cooling. The temperature was raised to 40° C. for 30 min. The reaction was poured into ice-water and the mixture was extracted with diethyl ether, washed twice with water, dried and evaporated. The solid residue (10 g) was chromatographed on silica gel using 10% ethyl acetate in benzene to afford 4.5 of white solid which was crystallized from butanol to give 9-phenylmethyl-1,3,4,9-tetrahydro-1,1-dimethylpyrano[3,4-b]indole, mp 132°-134° C.

Workup

  1. temperatureThe temperature was raised to 40° C. for 30 min
  2. extractionthe mixture was extracted with diethyl ether
  3. washwashed twice with water
  4. customdried
  5. customevaporated
  6. customThe solid residue (10 g) was chromatographed on silica gel using 10% ethyl acetate in benzene
  7. customto afford 4.5 of white solid which
  8. customwas crystallized from butanol

Sources & evidence

ORD record
ord-6755d7577a0341deb0d0cf10819f4798
Source dataset
uspto-grants-1980_10
Patent number
US04226860

Reaction notes

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