Methanol → 3-(2-(4-((4-Fluorophenyl)hydroxymethyl)-1-piperidinyl)ethyl)-2,4(1H,3H)-quinazolinedione

HRID 1156365Notes

Reaction equation

HRID 1156365 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][C:17]3=[O:27])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.CO.[BH4-].[Na+]>O>[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH:6]([OH:7])[CH:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][N:16]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[NH:18][C:17]3=[O:27])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3822KetanserinHCID 4311764Sodium borohydride

Product 1

HCID 1563943-(2-(4-((4-Fluorophenyl)hydroxymethyl)-1-piperidinyl)ethyl)-2,4(1H,3H)-quinazolinedione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 2.6 parts of 3-[2-[4-(4-fluorobenzoyl)-1-piperidinyl]ethyl]-2,4-(1H,3H)-quinazolinedione and 120 parts of methanol are added portionwise 2 parts of sodium borohydride. Upon completion, stirring is continued overnight at room temperature. Water is added and the whole is evaporated. The residue is stirred in water. The solid product is filtered off and crystallized from 2-propanone, yielding 1.2 parts of 3-[2-[4-[(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]ethyl]-2,4(1H,3H)-quinazolinedione; mp. 212.8° C.

Workup

  1. customthe whole is evaporated
  2. stirringThe residue is stirred in water
  3. filtrationThe solid product is filtered off
  4. customcrystallized from 2-propanone

Sources & evidence

ORD record
ord-45be1c0b95f7485189ed572b20128d75
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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