Hydrochloric Acid → 2-[5-(4-Fluorophenyl)-3-pyridylmethylaminomethyl]chroman hydrochloride

HRID 1825291Notes

Reaction equation

[ClH:1].[NH2:2][CH2:3][CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5]1.C[O-].[Na+].[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:25]=[C:26]([CH:30]=O)[CH:27]=[N:28][CH:29]=2)=[CH:20][CH:19]=1.[BH4-].[Na+].Cl>CO.O>[ClH:1].[F:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[CH:25]=[C:26]([CH2:30][NH:2][CH2:3][CH:4]3[CH2:13][CH2:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[O:5]3)[CH:27]=[N:28][CH:29]=2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

20.27 g of 2-aminomethylchroman hydrochloride are introduced into 130 g of methanol, and 20.4 g of a 30% sodium methoxide solution in methanol are subsequently added. 20.43 g of 5-(4-fluorophenyl)pyridine-3-carbaldehyde are added to the white suspension at 35° C., and the mixture is stirred for 1.5 hours before 4.20 g of sodium borohydride are added in portions. After 15 hours, 56.4 ml of water are added, and the pH of the mixture is adjusted to pH 2 using 37% hydrochloric acid. After the suspension has been cooled to 0° C., the crystals are filtered off, washed with methanol and dried under reduced pressure, giving 28.2 g of 2-[5-(4-fluorophenyl)-3-pyridylmethylaminomethyl]chroman hydrochloride (64% yield).

Workup

additionare subsequently added
additionare added in portions
filtrationthe crystals are filtered off
washwashed with methanol
customdried under reduced pressure

Sources & evidence

ORD record: ord-0e5ca059b7cb42afb5e2487cf0e705cc
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045629B2

Reaction notes

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