4-Fluorobenzoyl chloride → 3-[(4-Fluorobenzyl)methylamino]-8-fluoro-1,2,3,4-tetrahydrocarbazole

HRID 128131Notes

Reaction equation

HRID 128131 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][CH:6](O)[CH2:5][CH2:4]1.[F:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=O)=[CH:13][CH:12]=1.C[N:21]([CH:31]1[CH2:36][CH2:35][CH:34](O)[CH2:33][CH2:32]1)C(=O)C1C=CC(F)=CC=1.CN(C1CCC(=O)CC1)C(=O)C1C=CC([F:47])=CC=1>>[F:10][C:11]1[CH:19]=[CH:18][C:14]([CH2:15][CH2:1][NH:2][CH:3]2[CH2:8][C:7]3[C:36]4[C:31](=[C:32]([F:47])[CH:33]=[CH:34][CH:35]=4)[NH:21][C:6]=3[CH2:5][CH2:4]2)=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 678794-Fluorobenzoyl chlorideHCID 115718044-(Methylamino)cyclohexan-1-olHCID 128918784-(N-methyl-4-fluorobenzamido)-cyclohexanolHCID 128918804-(N-methyl-4-fluorobenzamido)-cyclohexanone

Product 1

HCID 569895323-[(4-Fluorobenzyl)methylamino]-8-fluoro-1,2,3,4-tetrahydrocarbazole

Procedure

Following procedures similar to those described in Example 260 there was obtained from 64.6 g. of 4-methylaminocyclohexanol, on reaction with 87.2 g. of 4-fluorobenzoyl chloride, 100.6 g. of 4-(N-methyl-4-fluorobenzamido)-cyclohexanol, m.p. 120°-130° C., 25.1 g. of which were oxidized to give 22.3 g. of 4-(N-methyl-4-fluorobenzamido)-cyclohexanone, m.p. 132°-136° C.

Workup

  1. customwas obtained from 64.6 g
  2. customto give 22.3 g

Sources & evidence

ORD record
ord-c57a1b9fefa64cf0a6532bc89c724ec8
Source dataset
uspto-grants-1981_03
Patent number
US04257952

Reaction notes

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